Substituted pyrimidinium compounds and derivatives for combating animal pests

ABSTRACT

The present invention relates to substituted pyrimidinium compounds of formula (I), to the stereoisomers, salts, tautomers and N-oxides thereof and to compositions comprising such compounds. The invention also relates to methods and uses of these substituted pyrimidinium compounds and of compositions thereof, for combating and controlling animal pests. Furthermore the invention relates also to pesticidal methods of applying such substituted pyrimidinium compounds. 
     The substituted pyrimidinium compounds of the present invention are defined by the following general formula (I) 
     
       
         
         
             
             
         
       
     
     wherein X, Y, Z, R 1 , R 2 , A and R 3  are defined as in the description.

The present invention relates to insecticidal substituted pyrimidiniumcompounds and/or to the compositions comprising such compounds forcombating invertebrate pests. The invention also relates to pesticidalmethods, to uses and to applications of substituted pyrimidiniumcompounds as described in the present invention and the stereoisomers,salts, tautomers and N-oxides thereof as well as compositions comprisingthem.

Invertebrate pests and in particular insects, arthropods and nematodesdestroy growing and harvested crops and attack wooden dwelling andcommercial structures, thereby causing large economic loss to the foodsupply and to property. While a large number of pesticidal agents areknown, due to the ability of target pests to develop resistance to saidagents, there is an ongoing need for new agents for combatinginvertebrate pests such as insects, arachnids and nematodes. It istherefore an object of the present invention to provide compounds havinga good pesticidal activity and showing a broad activity spectrum againsta large number of different invertebrate pests, especially againstdifficult to control insects, arachnids and nematodes.

It has been found that these objectives can be achieved by substitutedpyrimidinium compounds of the general formula (I), as defined below,including their stereoisomers, their salts, in particular theiragriculturally or veterinary acceptable salts, their tautomers and theirN-oxides.

Therefore, in a first aspect the present invention provides substitutedpyrimidinium compounds of formula (I) or a composition comprising atleast one substituted pyrimidinium compound of formula (I)

-   wherein-   X, Y are each independently O or S;-   Z is a direct bond, O, S(O)_(m), NR^(b), C(R^(a)R^(aa))O, C(═X¹),    C(═X¹)Y¹,or Y¹C(═X¹);-   X¹ is O, S, or NR^(b);-   Y¹ is O, S, or NR^(c);-   A is CH or N and, wherein the nitrogen of the pyrimidinium ring    taken together with the contiguous linking carbon atom and A as    depicted in formula (I), form a four- to seven-membered ring,    wherein each remaining ring member is selected from carbon atoms and    up to 3 heteroatoms independently selected from up to 2 O, up to 2    S, and up to 3 N(R^(c))_(p), wherein up to 2 carbon atom ring    members are independently selected from C(═O) and C(═S), and the    sulfur atom ring members are independently selected from S(═O)_(m),    wherein each ring may be substituted with up to 3 R^(a);-   R³ is C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₂-C₄-alkenyl,    C₂-C₄-haloalkenyl, C₂-C₄-alkynyl, C₂-C₄-haloalkynyl,    C₃-C₇-cycloalkyl, C₃-C₇-halocycloalkyl, C₄-C₈-alkylcycloalkyl,    C₄-C₈-haloalkylcycloalkyl, C₄-C₈-cycloalkylalkyl,    C₄-C₈-halocycloalkylalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,    C₂-C₆-alkylcarbonyl, C₂-C₆-haloalkylcarbonyl, each substituted with    at least one substituent selected from    -   CN, OR^(c), NR^(b)R^(c), NO₂, C(═O)(O)_(p)R^(c),        OC(═O)(O)_(p)R^(e), C(═O)NR^(b)R^(c), OC(═O)NR^(b)R^(e),        NR^(b)C(═O)(O)_(p)R^(e) NR^(b)C(═O)NR^(b)R^(c),        C(═S)NR^(b)R^(c), S(O),R^(b), SO₂NR^(b)R^(c), OSO₂R^(c),        OSO₂NR^(b)R^(c), NR^(b)SO₂R^(c), NR^(b)SO₂NR^(b)R^(c), SF₅, OCN,        SCN, Si(R^(d))₃, C(═N(O)_(p)R^(b))R^(b), C(═NNR^(b)R^(c))R^(b),        C(═NN(C(═O)O_(p)R^(c))R^(b))R^(b), ON═CR^(b)R^(c), ONR^(b)R^(c),        S(═O)_(o)(═NR^(b))_(q)R^(c), SO₂NR^(b)(═O)NR^(b)R^(c),        P(═X²)R^(b)R^(c), OP(═X²)(O_(p)R^(c))R^(b), OP(═X²)(OR^(c))₂,        N═CR^(b)R^(c), NR^(b)N═CR^(b)R^(c), NR^(b)NR^(b)R^(c),        NR^(b)C(═S)NR^(b)R^(c) NR^(b)C(═NR^(b))NR^(b)R^(c),        NR^(b)NR^(b)C(═X²)NR^(b)R^(c), NR^(b)NR^(b)SO₂NR^(b)R^(c), or        N═S(═O)_(p)R^(c)R^(c), or    -   two geminally bound groups R³ together may form a group selected        from ═O, ═S, ═CR^(b)R^(c), ═NR^(c), ═NOR^(c), and ═NNR^(c)R^(c);-   or R³ is phenyl optionally substituted with one or more substituents    selected from halogen, CN, OR^(c), NR^(b)R^(c), NO₂,    C(═O)(O)_(p)R^(c), OC(═O)(O)_(p)R^(e), C(═O)NR^(b)R^(c),    OC(═O)NR^(b)R^(e), NR^(b)C(═O)(O)_(p)R^(e) NR^(b)C(═O)NR^(b)R^(c),    C(═S)NR^(b)R^(c), S(O)_(m)R^(b), SO₂NR^(b)R^(c), OSO₂R^(c),    OSO₂NR^(b)R^(c), NR^(b)SO₂R^(c), NR^(b)SO₂NR^(b)R^(c), SF₅, OCN,    SCN, Si(R^(d))₃, C(═N(O)_(p)R^(b))R^(b), C(═NNR^(b)R^(c))R^(b),    C(═NN(C(═O)O_(p)R^(c))R^(b))R^(b), ON═CR^(b)R^(c), ONR^(b)R^(c),    S(═O)_(o)(═NR^(b))_(q)R^(c), SO₂NR^(b)(═O)NR^(b)R^(c),    P(═X²)R^(b)R^(c), OP(═X²)(O_(p)R^(c))R^(b), OP(═X²)(OR^(c))₂,    N═CR^(b)R^(c), NR^(b)N═CR^(b)R^(c), NR^(b)NR^(b)R^(c),    NR^(b)C(═S)NR^(b)R^(c) NR^(b)C(═NR^(b))NR^(b)R^(c),    NR^(b)NR^(b)C(═X²)NR^(b)R^(c), NR^(b)NR^(b)SO₂NR^(b)R^(c), or    N═S(═O)_(p)R^(c)R^(c),    -   or R³ is phenyl optionally substituted with one or more        substituents selected from C₁-C₄-alkyl, C₁-C₄-haloalkyl,        C₂-C₄-alkenyl, C₂-C₄-haloalkenyl, C₂-C₄-alkynyl,        C₂-C₄-haloalkynyl, C₃-C₇-cycloalkyl, C₃-C₇-halocycloalkyl,        C₄-C₈-alkylcycloalkyl, C₄-C₈-haloalkylcycloalkyl,        C₄-C₈-cycloalkylalkyl, C₄-C₈-halocycloalkylalkyl, C₁-C₆-alkoxy,        C₁-C₆-haloalkoxy, C₂-C₆-alkylcarbonyl, C₂-C₆-haloalkylcarbonyl,        which groups may optionally be substituted with halogen, CN,        OR^(c), NR^(b)R^(c), NO₂, C(═O)(O)_(p)R^(c), OC(═O)(O)_(p)R^(e),        C(═O)NR^(b)R^(c), OC(═O)NR^(b)R^(e), NR^(b)C(═O)(O)_(p)R^(e)        NR^(b)C(═O)NR^(b)R^(c), C(═S)NR^(b)R^(c), S(O)_(m)R^(b),        SO₂NR^(b)R^(c), OSO₂R^(c), OSO₂NR^(b)R^(c), NR^(b)SO₂R^(c),        NR^(b)SO₂NR^(b)R^(c), SF₅, OCN, SCN, Si(R^(d))₃,        C(═N(O)_(p)R^(b))R^(b), C(═NNR^(b)R^(c))R^(b),        C(═NN(C(═O)O_(p)R^(c))R^(b))R^(b), ON═CR^(b)R^(c), ONR^(b)R^(c),        S(═O)_(o)(═NR^(b))_(q)R^(c), SO₂NR^(b)(═O)NR^(b)R^(c),        P(═X²)R^(b)R^(c), OP(═X²)(O_(p)R^(c))R^(b), OP(═X²)(OR^(c))₂,        N═CR^(b)R^(c), NR^(b)N═CR^(b)R^(c), NR^(b)NR^(b)R^(c),        NR^(b)C(═S)NR^(b)R^(c) NR^(b)C(═NR^(b))NR^(b)R^(c),        NR^(b)NR^(b)C(═X²)NR^(b)R^(c), NR^(b)NR^(b)SO₂NR^(b)R^(c), or        N═S(═O)_(p)R^(c)R^(c);-   R¹ is hydrogen, C₁-C₈-alkyl, C₂-C₈-alkenyl, C₂-C₈-alkynyl,    C₃-C₁₀-cycloalkyl, C₄-C₁₀-cycloalkenyl, C₅-C₁₄-cycloalkylcycloalkyl    or R¹ may form a three- to eleven-membered saturated, or partially    unsaturated or aromatic carbo- or heterocyclic ring or ring system,    which may contain 1 to 4 heteroatoms selected from N(R^(e))_(p), O,    and S, wherein S may be oxidized, and wherein the aforementioned    groups and the carbo- or heterocyclic rings system may be    unsubstituted, partially or fully substituted with R^(a); or    -   R¹ is C(═O)R^(b), C(═O)OR^(e), NR^(b)R^(c), C(═O)NR^(b)R^(c),        C(═S)NR^(b)R^(c), SO₂NR^(b)R^(c), OC(═O)R^(c), OC(═O)OR^(e),        OC(═O)NR^(b)R^(e), N(R^(c))C(═O)R^(c), N(R^(c))C(═O)OR^(e),        N(R^(c))C(═O)NR^(b)R^(c), NR^(c)SO₂R^(b), NR^(c)SO₂NR^(b)R^(c),        Si(R^(d))₃, C(═NR^(c))R^(c), C(═NOR^(c))R^(c),        C(═NNR^(b)R^(c))R^(c), C(═NN(C(═O)R^(b))R^(c))R^(c),        C(═NN(C═O)OR^(c))(R^(c))₂, S(═O)_(o)(═NR^(b))_(q)R^(c), or        N═CR^(b)R^(c);-   R^(a) is each independently halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl,    C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₂-C₄-alkenyl, C₂-C₄-alkynyl,    C₃-C₆-cycloalkyl, CN, OR^(c), NR^(b)R^(c), NO₂, C(═O)(O)_(p)R^(c),    OC(═O)(O)_(p)R^(e), C(═O)NR^(b)R^(c), OC(═O)NR^(b)R^(e),    NR^(b)C(═O)(O)_(p)R^(e) NR^(b)C(═O)NR^(b)R^(c), C(═S)NR^(b)R^(c),    S(O)_(m)R^(b), SO₂NR^(b)R^(c), OSO₂R^(c), OSO₂NR^(b)R^(c),    NR^(b)SO₂R^(c), NR^(b)SO₂NR^(b)R^(c), N═S(═O)_(p)R^(c)R^(c),    S(═O)_(o)(═NR^(b))_(q)R^(c), SF₅, OCN, SCN, Si(R^(d))₃ or a three-    to six-membered saturated, or partially unsaturated or aromatic    carbo- or heterocyclic ring, which may contain 1 to 3 heteroatoms    selected from N—(R^(e))_(p), O, and S which may be oxidized, and    wherein the aforementioned groups and the carbo- or heterocyclic    ring may be partially or fully substituted with R^(aa), or two    geminally bound groups R^(a) together may form a group selected from    ═O, ═S, ═CR^(b)R^(c), ═NR^(c), ═NOR^(c), and ═NNR^(c)R^(c);    -   R^(aa) is each independently halogen, C₁-C₆-alkyl,        C₁-C₆-haloalkyl, C₁-C₆-alkoxy or C₁-C₆-haloalkoxy;-   R^(b) is each independently hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl,    C₁-C₆-alkoxy, C₁-C₆-haloalkoxy or a three- to six-membered    saturated, or partially unsaturated or aromatic carbo- or    heterocyclic ring, which may contain 1 to 3 heteroatoms selected    from N(R^(c))_(p), O, and S, wherein S may be oxidized and which    carbo- or heterocyclic ring may be partially or fully substituted    with R^(aa);-   R^(c) is each independently hydrogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl,    C₁-C₄-alkylcarbonyl, C₁-C₆ cycloalkyl, or a three- to six-membered    saturated, partially unsaturated or aromatic carbo- or heterocyclic    ring, which may contain 1 to 3 heteroatoms selected from    N(R^(aa))_(p), O and S, wherein S may be oxidized and wherein the    carbo- or heterocyclic ring may be partially or fully substituted    with R^(aa);-   wherein two geminally bound groups R^(b)R^(b), R^(c)R^(b) or    R^(c)R^(c) together with the atom to which they are bound, may form    a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or    aromatic carbo- or heterocyclic ring, which may contain 1 to 2    heteroatoms or heteroatoms groups selected from N, O, S, NO, SO and    SO₂ and wherein the carbo- or heterocyclic ring may be partially or    fully substituted with R⁴;-   R^(d) is each independently hydrogen, phenyl, C₁-C₆-alkyl,    C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₈-cycloalkyl, or    C₁-C₆-alkoxyalkyl, wherein the above mentioned groups may be    substituted with one or more halogen;-   R^(e) is each independently, C₁-C₄-alkyl, C₁-C₄-haloalkyl,    C₁-C₄-alkylcarbonyl, C₁-C₆ cycloalkyl, or a three- to six-membered    saturated, partially unsaturated or aromatic carbo- or heterocyclic    ring, which may contain 1 to 3 heteroatoms selected from    N(R^(aa))_(p), O and S, wherein S may be oxidized and wherein the    carbo- or heterocyclic ring may be partially or fully substituted    with R^(aa);-   n is 0, 1 or 2;-   m is 0, 1, or 2;-   p is 0 or 1;-   R² is H, halogen, CN, C₁-C₈ alkyl, C₂-C₈ alkenyl, C₂-C₈ alkynyl,    C₃-C₁₀ cycloalkyl, C₄-C₁₀ alkylcycloalkyl, C₄-C₁₀ cycloalkylalkyl,    C₆-C₁₄ cycloalkylcycloalkyl, C₅-C₁₀ alkylcycloalkylalkyl, or C₃-C₆    cycloalkenyl, wherein the aforementioned groups may be    unsubstituted, partially, or fully substituted with R^(2a), or R²    may form a carbo- or heterocyclic three- to ten-membered ring or a    seven- to eleven-membered rings system, which ring or ring system    may be saturated, partially unsaturated, or aromatic, and which ring    or ring system may contain 1 to 4 heteroatoms selected from    N(R^(e))_(p), O, and S, wherein S may be oxidized, and wherein the    carbo- or heterocyclic ring or rings system may be unsubstituted,    partially, or fully substituted with R^(2a);    -   with the proviso that if R² is halogen or CN, then Z is a direct        bond;    -   R^(2a) is each independently halogen, C₁-C₆-alkyl,        C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₂-C₄-alkenyl,        C₂-C₄-alkynyl, C₃-C₆-cycloalkyl, CN, OR^(c), NR^(b)R^(c), NO₂,        C(═O)(O)_(p)R^(c), OC(═O)(O)_(p)R^(e), C(═O)NR^(b)R^(c),        OC(═O)NR^(b)R^(e), NR^(b)C(═O)(O)_(p)R^(e)        NR^(b)C(═O)NR^(b)R^(c), C(═S)NR^(b)R^(c), S(O)_(m)R^(b),        SO₂NR^(b)R^(c), OSO₂R^(c), OSO₂NR^(b)R^(c), NR^(b)SO₂R^(c),        NR^(b)SO₂NR^(b)R^(c), SF₅, OCN, SCN, Si(R^(d))₃,        C(═N(O)_(p)R^(b)) R^(b), C(═NNR^(b)R^(c))R^(b),        C(═NN(C(═O)O_(p)R^(c))R^(c))R^(b), ON═CR^(b)R^(c), ONR^(b)R^(c),        S(═O)_(o)(═NR^(b))_(q)R^(c), SO₂NR^(b)(═O)NR^(b)R^(c),        P(═X²)R^(b)R^(c), OP(═X²)(O_(p)R^(c))R^(b), OP(═X²)(OR^(c))₂,        N═CR^(b)R^(c), NR^(b)N═CR^(b)R^(c), NR^(b)NR^(b)R^(c),        NR^(b)C(═S)NR^(b)R^(c) NR^(b)C(═NR^(b))NR^(b)R^(c),        NR^(b)NR^(b)C(═X²)NR^(b)R^(c), NR^(b)NR^(b)SO₂NR^(b)R^(c),        N═S(═O)_(p)R^(c)R^(c), or a three- to six-membered saturated, or        partially unsaturated or aromatic carbo- or heterocyclic ring,        which may contain 1 to 3 heteroatoms selected from        N—(R^(c))_(p), O, and S, wherein S may be oxidized, and wherein        the aforementioned groups and the carbo- or heterocyclic ring        may be partially or fully substituted with R^(2aa); or    -   two geminally bound groups R^(2a) together may form a group        selected from ═O, ═S, ═CR^(b)R^(c), ═NR^(c), ═NOR^(c), and        ═NNR^(c)R^(c);    -   R^(2aa) is each independently halogen, C₁-C₆-alkyl,        C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₂-C₄-alkenyl,        C₂-C₄-alkynyl, C₃-C₆-cycloalkyl, CN, OR^(c), NR^(b)R^(c), NO₂,        C(═O)(O)_(p)R^(c), OC(═O)(O)_(p)R^(e), C(═O)NR^(b)R^(c),        OC(═O)NR^(b)R^(e), NR^(b)C(═O)(O)_(p)R^(e)        NR^(b)C(═O)NR^(b)R^(c), C(═S)NR^(b)R^(c), S(O)_(m)R^(b),        SO₂NR^(b)R^(c), OSO₂R^(c), OSO₂NR^(b)R^(c), NR^(b)SO₂R^(c),        NR^(b)SO₂NR^(b)R^(c), SF₅, OCN, SCN, Si(R^(d))₃,        C(═N(O)_(p)R^(b))R^(b), C(═NNR^(b)R^(c))R^(b),        C(═NN(C(═O)O_(p)R^(c))R^(b))R^(b), ON═CR^(b)R^(c), ONR^(b)R^(c),        S(═O)_(o)(═NR^(b))_(q)R^(c), SO₂NR^(b)(═O)NR^(b)R^(c),        P(═X²)R^(b)R^(c), OP(═X²)(O_(p)R^(c))R^(b), OP(═X²)(OR^(c))₂,        N═CR^(b)R^(c), NR^(b)N═CR^(b)R^(c), NR^(b)NR^(b)R^(c),        NR^(b)C(═S)NR^(b)R^(c), NR^(b)C(═NR^(b))NR^(b)R^(c),        NR^(b)NR^(b)C(═X²)NR^(b)R^(c), NR^(b)NR^(b)SO₂NR^(b)R^(c), or        N═S(═O)_(p)R^(c)R^(c), or        -   two geminally bound groups R^(2aa) together may form a group            selected from ═O, ═S, ═CR^(b)R^(c), ═NR^(c), ═NOR^(c), and            ═NNR^(c)R^(c);    -   X² is independently O or S;    -   R⁴ is each independently halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl,        C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₂-C₄-alkenyl, C₂-C₄-alkynyl,        C₃-C₆-cycloalkyl, CN, OR^(c), NR^(b)R^(c), NO₂,        C(═O)(O)_(p)R^(c), OC(═O)(O)_(p)R^(e), C(═O)NR^(b)R^(c),        OC(═O)NR^(b)R^(e), NR^(b)C(═O)(O)_(p)R^(e)        NR^(b)C(═O)NR^(b)R^(c), C(═S)NR^(b)R^(c), S(O),R^(b),        SO₂NR^(b)R^(c), OSO₂R^(c), OSO₂NR^(b)R^(c), NR^(b)SO₂R^(c),        NR^(b)SO₂NR^(b)R^(c), SF₅, OCN, SCN, Si(R^(d))₃,        C(═N(O)_(p)R^(b))R^(b), C(═NNR^(b)R^(c))R^(b),        C(═NN(C(═O)O_(p)R^(c))R^(b))R^(b), ON═CR^(b)R^(c), ONR^(b)R^(c),        S(═O)_(o)(═NR^(b))_(q)R^(c), SO₂NR^(b)(═O)NR^(b)R^(c),        P(═X²)R^(b)R^(c), OP(═X²)(O_(p)R^(c))R^(b), OP(═X²)(OR^(c))₂,        N═CR^(b)R^(c), NR^(b)N═CR^(b)R^(c), NR^(b)NR^(b)R^(c),        NR^(b)C(═S)NR^(b)R^(c) NR^(b)C(═NR^(b))NR^(b)R^(c),        NR^(b)NR^(b)C(═X²)NR^(b)R^(c), NR^(b)NR^(b)SO₂NR^(b)R^(c), or        N═S(═O)_(p)R^(c)R^(c), or        -   two geminally bound groups R⁴ together may form a group            selected from ═O, ═S, ═CR^(b)R^(c), ═NR^(c), ═NOR^(c), and            ═NNR^(c)R^(c);            or a stereoisomer, tautomer, salt, or N-oxide thereof.

WO2014/167084 describes certain substituted pyrimidinium compounds withheterocyclic substituents for combating invertebrate pests.

WO2016/171053 describes certain substituted pyrido[1,2-a]pyrimidiniumcompounds.

The substituted pyrimidinium compounds of formula (I) according to thepresent invention, with their characteristic substitution pattern, havenot yet been described for pesticidal uses or pesticidal applications inagricultural industry or veterinary practice.

The substituted pyrimidinium compounds of the formula (I), and theiragriculturally acceptable salts are highly active against animal pest,i.e. harmful arthropodes and nematodes, especially against insects andacaridae which are difficult to control by other means.

Moreover, the present invention relates to and includes the followingembodiments:

-   -   compositions comprising at least one compound of formula (I) as        defined above;    -   agricultural and veterinary compositions comprising an amount of        at least one compound of formula (I) or an enantiomer,        diasteromer or salt thereof as defined above;    -   a method for combating invertebrate pests, infestation, or        infection by invertebrate pests, which method comprises        contacting said pest or its food supply, habitat or breeding        grounds with a pesticidally effective amount of at least one        compound of formula (I) as defined above or a composition        thereof;    -   a method for controlling invertebrate pests, infestation, or        infection by invertebrate pests, which method comprises        contacting said pest or its food supply, habitat or breeding        grounds with a pesticidally effective amount of at least one        compound of formula (I) as defined above or a composition        comprising at least one compound of formula (I);    -   a method for preventing or protecting against invertebrate pests        comprising contacting the invertebrate pests, or their food        supply, habitat or breeding grounds with a substituted        pyrimidinium compounds of the general formula (I) as defined        above or a composition comprising at least one compound of        formula (I) as defined above or a composition comprising at        least one compound of formula (I);    -   a method for protecting crops, plants, plant propagation        material and/or growing plants from attack or infestation by        invertebrate pests comprising contacting or treating the crops,        plants, plant propagation material and growing plants, or soil,        material, surface, space, area or water in which the crops,        plants, plant propagation material is stored or the plant is        growing, with a pesticidally effective amount of at least one        compound of formula (I) as defined above or a composition        comprising at least one compound of formula (I);    -   a non-therapeutic method for treating animals infested or        infected by parasites or preventing animals of getting infected        or infested by parasites or protecting animals against        infestation or infection by parasites which comprises orally,        topically or parenterally administering or applying to the        animals a parasiticidally effective amount of a compound of        formula (I) as defined above or a composition comprising at        least one compound of formula (I);    -   a method for treating, controlling, preventing or protecting        animals against infestation or infection by parasites by        administering or applying orally, topically or parenterally to        the animals a substituted pyrimidinium compound of the general        formula (I) as defined above or a composition comprising at        least one compound of formula (I);    -   seed comprising a compound of formula (I) as defined above, in        an amount of from 0.1 g to 10 kg per 100 kg of seed;    -   the use of the compounds of formula (I) as defined above for        protecting growing plants or plant propagation material from        attack or infestation by invertebrate pests;    -   the use of compounds of formula (I) or the enantiomers,        diastereomers or veterinary acceptable salts thereof for        combating parasites in and on animals;    -   a process for the preparation of a veterinary composition for        treating, controlling, preventing or protecting animals against        infestation or infection by parasites which comprises adding a        parasiticidally effective amount of an compound of formula (I)        or the enantiomers, diastereomers and/or veterinary acceptable        salt thereof to a carrier composition suitable for veterinary        use;    -   the use of a compound of formula (I) or the enantiomers,        diastereomers and/or veterinary acceptable salt thereof for the        preparation of a medicament for treating, controlling,        preventing or protecting animals against infestation or        infection by parasites.

All the compounds of the present invention including if applicable theirstereoisomers, their tautomers, their salts or their N-oxides as well ascompositions thereof are particularly useful for controllinginvertebrate pests, in particular for controlling arthropods andnematodes and especially insects. Therefore, the invention relates tothe use of a compound as disclosed in the present invention, forcombating or controlling invertebrate pests, in particular invertebratepests of the group of insects, arachnids or nematodes.

The term “compound(s) according to the invention” or “compound(s) offormula (I)” as used in the present invention refers to and comprisesthe compound(s) as defined herein and/or stereoisomer(s), salt(s),tautomer(s) or N-oxide(s) thereof. The term “compound(s) of the presentinvention” is to be understood as equivalent to the term “compound(s)according to the invention” therefore also comprising stereoisomer(s),salt(s), tautomer(s) or N-oxide(s) of compounds of formula (I).

The term composition(s) according to the invention or “composition(s) ofthe present invention” encompasses composition(s) comprising at leastone compound of formula (I) according to the invention as defined above,therefore also including a stereoisomer, an agriculturally or veterinaryacceptable salt, tautomer or an N-oxide of the compounds of formula (I).

The compounds of the formula (I) are present in mesomeric forms.

These forms may be expressed in different isoelectronic formulae, eachhaving the formal positive and negative charges on different atoms (asshown below). The present invention extends to all representativeisoelectronic structures of compounds of formula I.

The compounds of the formula (I) have one or more centers of chirality,i.e. they are present as mixtures of enantiomers or diastereomers. Theinvention provides both the single pure enantiomers or purediastereomers of the compounds of formula (I), and their mixtures andthe use according to the invention of the pure enantiomers or purediastereomers of the compound of formula (I) or its mixtures. Suitablecompounds of the formula (I) also include all possible geometricalstereoisomers (cis/trans isomers) and mixtures thereof. Cis/transisomers may be present with respect to an alkene, carbon-nitrogendouble-bond or amide group. The term “stereoisomer(s)” encompasses bothoptical isomers, such as enantiomers or diastereomers, the latterexisting due to more than one center of chirality in the molecule, aswell as geometrical isomers (cis/trans isomers). The present inventionrelates to every possible stereoisomer of the compounds of formula (I),i.e. to single enantiomers or diastereomers, as well as to mixturesthereof.

In one embodiment of the invention, the compounds of formula (I) havethe following stereochemistry as in formula (I-R):

In another embodiment of the invention, the compounds of formula (I)have the following stereochemistry as in formula (I-S):

The compounds of the present invention may be amorphous or may exist inone or more different crystalline states (polymorphs) or modificationswhich may have a different macroscopic properties such as stability orshow different biological properties such as activities. The presentinvention includes both amorphous and crystalline compounds of theformula (I), mixtures of different crystalline states or modificationsof the respective compound I, as well as amorphous or crystalline saltsthereof.

Salts of the compounds of the formula (I) are preferably agriculturallyand/or veterinary acceptable salts. They can be formed in a customarymethod, e.g. by reacting the compound with an acid of the anion inquestion if the compound of formula (I) has a basic functionality or byreacting an acidic compound of formula (I) with a suitable base.

Suitable agriculturally or veterinary useful salts are especially thesalts of those cations or the acid addition salts of those acids whosecations and anions, respectively, do not have any adverse effect on theaction of the compounds according to the present invention. Suitablecations are in particular the ions of the alkali metals, preferablylithium, sodium and potassium, of the alkaline earth metals, preferablycalcium, magnesium and barium, and of the transition metals, preferablymanganese, copper, zinc and iron, and also ammonium (NH₄ ⁺) andsubstituted ammonium in which one to four of the hydrogen atoms arereplaced by C₁-C₄-alkyl, C₁-C₄-hydroxyalkyl, C₁-C₄-alkoxy, C₁-C₄-alkoxy,hydroxy-C₁-C₄-alkoxy-C₁-C₄-alkyl, phenyl or benzyl. Examples ofsubstituted ammonium ions comprise methylammonium, isopropylammonium,dimethylammonium, diisopropylammonium, trimethylammonium,tetramethylammonium, tetraethylammonium, tetrabutylammonium,2-hydroxyethylammonium, 2-(2-hydroxyethoxy)ethyl-ammonium,bis(2-hydroxyethyl)ammonium, benzyltrimethylammonium andbenzyltriethylammonium, furthermore phosphonium ions, sulfonium ions,preferably tri(C₁-C₄-alkyl)sulfonium, and sulfoxonium ions, preferablytri(C₁-C₄-alkyl)sulfoxonium.

Anions of useful acid addition salts are primarily chloride, bromide,fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogenphosphate, phosphate, nitrate, hydrogen carbonate, carbonate,hexafluorosilicate, hexafluorophosphate, benzoate, and the anions ofC₁-C₄-alkanoic acids, preferably formate, acetate, propionate andbutyrate. They can be formed by reacting the compounds of the formulae Iwith an acid of the corresponding anion, preferably of hydrochloricacid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.

The term “N-oxide” includes any compound of the present invention whichhas at least one tertiary nitrogen atom that is oxidized to an N-oxidemoiety.

The organic moieties groups mentioned in the above definitions of thevariables are—like the term halogen—collective terms for individuallistings of the individual group members. The prefix C_(n)-C_(m)indicates in each case the possible number of carbon atoms in the group.

“Halogen” will be taken to mean fluoro, chloro, bromo and iodo.

The term “partially or fully halogenated” will be taken to mean that 1or more, e.g. 1, 2, 3, 4 or 5 or all of the hydrogen atoms of a givenradical have been replaced by a halogen atom, in particular by fluorineor chlorine.

The term “C_(n)-C_(m)-alkyl” as used herein (and also inC_(n)-C_(m)-alkylamino, di-C_(n)-C_(m)-alkylamino,C_(n)-C_(m)-alkylaminocarbonyl, di-(C_(n)-C_(m)-alkylamino)carbonyl,C_(n)-C_(m)-alkylsulfinyl and C_(n)-C_(m)-alkylsulfonyl) refers to abranched or unbranched saturated hydrocarbon group having n to m, e.g. 1to 10 carbon atoms, preferably 1 to 6 carbon atoms, for example methyl,ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl,1,1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl,2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1,1-dimethylpropyl,1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl,4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl,2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl,2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl,1-ethyl-1-methylpropyl, 1-ethyl-2-methylpropyl, heptyl, octyl,2-ethylhexyl, nonyl and decyl and their isomers. C₁-C₄-alkyl means forexample methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl,2-methylpropyl or 1,1-dimethylethyl.

The term “C_(n)-C_(m)-haloalkyl” as used herein (and also inC_(n)-C_(m)-haloalkylsulfinyl and C_(n)-C_(m)-haloalkylsulfonyl) refersto a straight-chain or branched alkyl group having n to m carbon atoms,e.g. 1 to 10 in particular 1 to 6 carbon atoms (as mentioned above),where some or all of the hydrogen atoms in these groups may be replacedby halogen atoms as mentioned above, for example C₁-C₄-haloalkyl, suchas chloromethyl, bromomethyl, dichloromethyl, trichloromethyl,fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl,dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl,1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl,2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl,2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl andthe like. The term C₁-C₁₀-haloalkyl in particular comprisesC₁-C₂-fluoroalkyl, which is synonym with methyl or ethyl, wherein 1, 2,3, 4 or 5 hydrogen atoms are substituted by fluorine atoms, such asfluoromethyl, difluoromethyl, trifluoromethyl, 1-fluoroethyl,2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl andpentafluoromethyl.

Similarly, “C_(n)-C_(m)-alkoxy” and “C_(n)-C_(m)-alkylthio” (orC_(n)-C_(m)-alkylsulfenyl, respectively) refer to straight-chain orbranched alkyl groups having n to m carbon atoms, e.g. 1 to 10, inparticular 1 to 6 or 1 to 4 carbon atoms (as mentioned above) bondedthrough oxygen (or sulfur linkages, respectively) at any bond in thealkyl group. Examples include C₁-C₄-alkoxy such as methoxy, ethoxy,propoxy, isopropoxy, butoxy, sec-butoxy, isobutoxy and tert-butoxy,further C₁-C₄-alkylthio such as methylthio, ethylthio, propylthio,isopropylthio, and n-butylthio.

Accordingly, the terms “C_(n)-C_(m)-haloalkoxy” and“C_(n)-C_(m)-haloalkylthio” (or C_(n)-C_(m)-haloalkyl-sulfenyl,respectively) refer to straight-chain or branched alkyl groups having nto m carbon atoms, e.g. 1 to 10, in particular 1 to 6 or 1 to 4 carbonatoms (as mentioned above) bonded through oxygen or sulfur linkages,respectively, at any bond in the alkyl group, where some or all of thehydrogen atoms in these groups may be replaced by halogen atoms asmentioned above, for example C₁-C₂-haloalkoxy, such as chloromethoxy,bromomethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy,difluoromethoxy, trifluoromethoxy, chlorofluoromethoxy,dichlorofluoromethoxy, chlorodifluoromethoxy, 1-chloroethoxy,1-bromoethoxy, 1-fluoroethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy,2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy,2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy,2,2,2-trichloroethoxy and pentafluoroethoxy, furtherC₁-C₂-haloalkylthio, such as chloromethylthio, bromomethylthio,dichloromethylthio, trichloromethylthio, fluoromethylthio,difluoromethylthio, trifluoromethylthio, chlorofluoromethylthio,dichlorofluoromethylthio, chlorodifluoromethylthio, 1-chloroethylthio,1-bromoethylthio, 1-fluoroethylthio, 2-fluoroethylthio,2,2-difluoroethylthio, 2,2,2-trifluoroethylthio,2-chloro-2-fluoroethylthio, 2-chloro-2,2-difluoroethylthio,2,2-dichloro-2-fluoroethylthio, 2,2,2-trichloroethylthio andpentafluoroethylthio and the like. Similarly the termsC₁-C₂-fluoroalkoxy and C₁-C₂-fluoroalkylthio refer to C₁-C₂-fluoroalkylwhich is bound to the remainder of the molecule via an oxygen atom or asulfur atom, respectively.

The term “C₂-C_(m)-alkenyl” as used herein intends a branched orunbranched unsaturated hydrocarbon group having 2 to m, e.g. 2 to 10 or2 to 6 carbon atoms and a double bond in any position, such as ethenyl,1-propenyl, 2-propenyl, 1-methyl-ethenyl, 1-butenyl, 2-butenyl,3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl,1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl,3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl,3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl,3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl,3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl,1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl,1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl,1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl,4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl,3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl,2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl,1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl,4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl,1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl,1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl,2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl,2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl,1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl,2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl,1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl,1-ethyl-2-methyl-1-propenyl and 1-ethyl-2-methyl-2-propenyl.

The term “C₂-C_(m)-alkynyl” as used herein refers to a branched orunbranched unsaturated hydrocarbon group having 2 to m, e.g. 2 to 10 or2 to 6 carbon atoms and containing at least one triple bond, such asethynyl, propynyl, 1-butynyl, 2-butynyl, and the like.

The term “C_(n)-C_(m)-alkoxy-C_(n)-C_(m)-alkyl” as used herein refers toalkyl having n to m carbon atoms, e.g. like specific examples mentionedabove, wherein one hydrogen atom of the alkyl radical is replaced by anC_(n)-C_(m)-alkoxy group; wherein the value of n and m of the alkoxygroup are independently chosen from that of the alkyl group.

The suffix “-carbonyl” in a group or “C(═O)” denotes in each case thatthe group is bound to the remainder of the molecule via a carbonyl C═Ogroup. This is the case e.g. in alkylcarbonyl, haloalkylcarbonyl,aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkoxycarbonyl,haloalkoxycarbonyl.

The term “aryl” as used herein refers to a mono-, bi- or tricyclicaromatic hydrocarbon radical such as phenyl or naphthyl, in particularphenyl (also referred as to C₆H₅ as substituent).

The term “ring system” denotes two or more directly connected rings.

The term “C₃-C_(m)-cycloalkyl” as used herein refers to a monocyclicring of 3- to m-membered saturated cycloaliphatic radicals, e.g.cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl,cyclooctyl and cyclodecyl.

The term “alkylcycloalkyl” denotes as well as the term “alkyl which maybe substituted with cycloalkyl” an alkyl group which is substituted witha cycloalkyl ring, wherein alkyl and cycloakyl are as herein defined.

The term “cycloalkylalkyl” denotes as well as the term “cycloalkyl whichmay be substituted with alkyl” a cycloalkyl ring which is substitutedwith an alkyl group, wherein alkyl and cycloakyl are as herein defined.

The term “alkylcycloalkylalkyl” denotes as well as the term“alkylcycloalkyl which may be substituted with alkyl” an alkylcycloalkylgroup which is substituted with an alkyl, wherein alkyl andalkylcycloakyl are as herein defined.

The term “C₃-C_(m)-cycloalkenyl” as used herein refers to a monocyclicring of 3- to m-membered partially unsaturated cycloaliphatic radicals.

The term “cycloalkylcycloalkyl” denotes as well as the term “cycloalkylwhich may be substituted with cycloalkyl” a cycloalkyl substitution onanother cycloalkyl ring, wherein each cycloalkyl ring independently hasfrom 3 to 7 carbon atom ring members and the cycloalkyls are linkedthrough one single bond or have one common carbon atom. Examples ofcycloalkylcycloalkyl include cyclopropylcyclopropyl (e.g.1,1′-bicyclopropyl-2-yl), cyclohexylcyclohexyl wherein the two rings arelinked through one single common carbon atom (e.g.1,1′-bicyclohexyl-2-yl), cyclohexylcyclopentyl wherein the two rings arelinked through one single bond (e.g. 4-cyclopentylcyclohexyl) and theirdifferent stereoisomers such as (1R,2S)-1, 1′-bicyclopropyl-2-yl and(1R,2R)-1,1′-bicyclopropyl-2-yl.

The term “3- to 6-membered carbocyclic ring” as used herein refers tocyclopropane, cyclobutane, cyclopentane and cyclohexane rings.

The term “3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturatedor aromatic heterocyclic ring which may contain 1, 2, 3 or 4heteroatoms” or “containing heteroatom groups”, wherein thoseheteroatom(s) (group(s)) are selected from N (N-substituted groups), Oand S (S-substituted groups) as used herein refers to monocyclicradicals, the monocyclic radicals being saturated, partially unsaturatedor aromatic (completely unsaturated). The heterocyclic radical may beattached to the remainder of the molecule via a carbon ring member orvia a nitrogen ring member.

Examples of 3-, 4-, 5-, 6- or 7-membered saturated heterocyclyl orheterocyclic rings include: oxiranyl, aziridinyl, azetidinyl,2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl,3-tetrahydrothienyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-pyrazolidinyl,4-pyrazolidinyl, 5-pyrazolidinyl, 2-imidazolidinyl, 4-imidazolidinyl,2-oxazolidinyl, 4-oxazolidinyl, 5-oxazolidinyl, 3-isoxazolidinyl,4-isoxazolidinyl, 5-isoxazolidinyl, 2-thiazolidinyl, 4-thiazolidinyl,5-thiazolidinyl, 3-isothiazolidinyl, 4-isothiazolidinyl,5-isothiazolidinyl, 1,2,4-oxadiazolidin-3-yl, 1,2,4-oxadiazolidin 5 yl,1,2,4-thiadiazolidin-3-yl, 1,2,4-thiadiazolidin-5-yl,1,2,4-triazolidin-3-yl-1,3,4-oxadiazolidin-2-yl,1,3,4-thiadiazolidin-2-yl, 1,3,4-triazolidin-2-yl, 2-tetrahydropyranyl,4-tetrahydropyranyl, 1,3-dioxan-5-yl, 1,4-dioxan-2-yl, 2-piperidinyl,3-piperidinyl, 4-piperidinyl, 3-hexahydropyridazinyl,4-hexahydropyridazinyl, 2-hexahydropyrimidinyl, 4-hexahydropyrimidinyl,5-hexahydropyrimidinyl, 2-piperazinyl, 1,3,5-hexahydrotriazin-2-yl and1,2,4-hexahydrotriazin-3-yl, 2-morpholinyl, 3-morpholinyl,2-thiomorpholinyl, 3-thiomorpholinyl, 1-oxothiomorpholin-2-yl,1-oxothiomorpholin-3-yl, 1,1-dioxothiomorpholin-2-yl,1,1-dioxothiomorpholin-3-yl, hexahydroazepin-1-, -2-, -3- or -4-yl,hexahydrooxepinyl, hexahydro-1,3-diazepinyl, hexahydro-1,4-diazepinyl,hexahydro-1,3-oxazepinyl, hexahydro-1,4-oxazepinyl,hexahydro-1,3-dioxepinyl, hexahydro-1,4-dioxepinyl and the like.Examples of 3-, 4-, 5-, 6- or 7-membered partially unsaturatedheterocyclyl or heterocyclic rings include: 2,3-dihydrofur-2-yl,2,3-dihydrofur-3-yl, 2,4-dihydrofur-2-yl, 2,4-dihydrofur-3-yl,2,3-dihydrothien-2-yl, 2,3-dihydrothien-3-yl, 2,4-dihydrothien-2-yl,2,4-dihydrothien-3-yl, 2-pyrrolin-2-yl, 2-pyrrolin-3-yl,3-pyrrolin-2-yl, 3-pyrrolin-3-yl, 2-isoxazolin-3-yl, 3-isoxazolin-3-yl,4-isoxazolin 3 yl, 2-isoxazolin-4-yl, 3-isoxazolin-4-yl,4-isoxazolin-4-yl, 2-isoxazolin-5-yl, 3-isoxazolin-5-yl,4-isoxazolin-5-yl, 2-isothiazolin-3-yl, 3-isothiazolin-3-yl,4-isothiazolin-3-yl, 2-isothiazolin-4-yl, 3-isothiazolin-4-yl,4-isothiazolin-4-yl, 2-isothiazolin-5-yl, 3-isothiazolin-5-yl,4-isothiazolin-5-yl, 2,3 dihydropyrazol-1-yl, 2,3-dihydropyrazol-2-yl,2,3-dihydropyrazol-3-yl, 2,3-dihydropyrazol-4-yl,2,3-dihydropyrazol-5-yl, 3,4-dihydropyrazol-1-yl,3,4-dihydropyrazol-3-yl, 3,4-dihydropyrazol-4-yl,3,4-dihydropyrazol-5-yl, 4,5-dihydropyrazol-1-yl,4,5-dihydropyrazol-3-yl, 4,5-dihydropyrazol-4-yl,4,5-dihydropyrazol-5-yl, 2,3-dihydrooxazol-2-yl, 2,3-dihydrooxazol-3-yl,2,3-dihydrooxazol-4-yl, 2,3-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl,3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, 3,4-dihydrooxazol-5-yl,3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl,2-, 3-, 4-, 5- or 6-di- or tetrahydropyridinyl, 3-di- ortetrahydropyridazinyl, 4-di- or tetrahydropyridazinyl, 2-di- ortetrahydropyrimidinyl, 4-di- or tetrahydropyrimidinyl, 5-di- ortetrahydropyrimidinyl, di- or tetrahydropyrazinyl, 1,3,5-di- ortetrahydrotriazin-2-yl, 1,2,4-di- or tetrahydrotriazin-3-yl,2,3,4,5-tetrahydro[1H]azepin-1-, -2-, -3-, -4-, -5-, -6- or -7-yl,3,4,5,6-tetrahydro[2H]azepin-2-, -3-, -4-, -5-, -6- or -7-yl, 2,3,4,7tetrahydro[1H]azepin-1-, -2-, -3-, -4-, -5-, -6- or -7-yl, 2,3,6,7tetrahydro[1H]azepin-1-, -2-, -3-, -4-, -5-, -6- or -7-yl,tetrahydrooxepinyl, such as 2,3,4,5-tetrahydro[1H]oxepin 2, 3, 4, 5, 6or -7 yl, 2,3,4,7 tetrahydro[1H]oxepin-2-, -3-, -4-, -5-, -6- or -7-yl,2,3,6,7 tetrahydro[1H]oxepin-2-, -3-, -4-, -5-, -6- or -7-yl,tetrahydro-1,3-diazepinyl, tetrahydro-1,4-diazepinyl,tetrahydro-1,3-oxazepinyl, tetrahydro-1,4-oxazepinyl,tetrahydro-1,3-dioxepinyl and tetrahydro-1,4-dioxepinyl.

Examples of 5- or 6-membered aromatic heterocyclic (hetaryl) orheteroaromatic rings are: 2-furyl, 3-furyl, 2-thienyl, 3-thienyl,2-pyrrolyl, 3-pyrrolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl,2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl,5-thiazolyl, 2-imidazolyl, 4-imidazolyl, 1,3,4-triazol-2-yl,2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyridazinyl, 4-pyridazinyl,2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl and 2-pyrazinyl.

A “C₂-C_(m)-alkylene” is divalent branched or preferably unbranchedsaturated aliphatic chain having 2 to m, e.g. 2 to 7 carbon atoms, forexample CH₂CH₂, —CH(CH₃)—, CH₂CH₂CH₂, CH(CH₃)CH₂, CH₂CH(CH₃),CH₂CH₂CH₂CH₂, CH₂CH₂CH₂CH₂CH₂, CH₂CH₂CH₂CH₂CH₂CH₂, andCH₂CH₂CH₂CH₂CH₂CH₂CH₂.

Embodiments and preferred compounds of the present invention for use inpesticidal methods and for insecticidal application purposes areoutlined in the following paragraphs.

The remarks made below concerning preferred embodiments of the variables(substituents) of the compounds according to the invention, especiallywith respect to their substituents X, Y, Z, X¹, X², Y¹, A, R¹, R^(a),R^(aa), R^(b), R^(c), R^(d), R^(e), R², R^(2a), R^(2aa), R⁴, m, n, p andR³ are valid both on their own and, in particular, in every possiblecombination with each other and where applicable, the uses, the methodsand the compositions according to the invention.

In a particular embodiment, the variables of the compounds of formula(I) have the following meanings, these meanings, both on their own andin combination with one another, being particular embodiments of thecompounds of the formula (I):

In one preferred embodiment of the compounds of formula (I), X is O.These compounds correspond to the compounds of formula (I.1).

In a further embodiment of the compounds of the formula (I), X is S.These compounds correspond to the compounds of formula (I.2).

In another embodiment of the compounds of formula (I), Y is S. Thesecompounds correspond to the compounds of formula (I.A).

In another embodiment of the compounds of formula (I), Y is O. Thesecompounds correspond to the compounds of formula (I.B).

In another embodiment of the compounds of formula (I), Y is S and X isO. These compounds correspond to compounds of formula I.1.A:

In another embodiment of the compounds of formula (I), Y is S and X isS. These compounds correspond to compounds of formula I.2.A.

In another embodiment of the compounds of formula (I), Y is O and X isO. These compounds correspond to compounds of formula I.1.B.

In another embodiment of the compounds of formula (I), Y is O and X isS. These compounds correspond to compounds of formula I.2.B.

Within these embodiments, compounds of formula I.1.B are preferred.

In an embodiment of the compounds of formula (I), Z is a direct bond orC(R^(a)R^(aa))O.

In a further embodiment of the compounds of formula (I), Z is a directbond.

In an embodiment of the compounds of formula (I), Z is O, S(O)_(m),NR^(b), C(═X¹), C(═X¹)Y¹, or Y¹C(═X¹). In a further embodiment, Z is O,S(O)_(m), or NR^(b). In another embodiment, Z is C(═X¹), C(═X¹)Y¹, orY¹C(═X¹).

In an embodiment of the compounds of formula (I), X¹ is O.

In an embodiment of the compounds of formula (I), X¹ is S.

In an embodiment of the compounds of formula (I), X¹ is NR^(b).

In an embodiment of the compounds of formula (I), Y¹ is O.

In an embodiment of the compounds of formula (I), Y¹ is S.

In an embodiment of the compounds of formula (I), Y¹ is NR^(c).

In an embodiment of the compounds of formula (I), A is CH or N and,wherein the nitrogen of the pyrimidinium ring taken together with thecontiguous linking carbon atom and A as depicted in formula (I), form afour- to seven-membered ring, wherein such ring is not an aromatic ring,and wherein each remaining ring member is selected from carbon atoms andup to 3 heteroatoms independently selected from up to 2 O, up to 2 S,and up to 3 N(R^(c))_(p), wherein up to 2 carbon atom ring members areindependently selected from C(═O) and C(═S), and the sulfur atom ringmembers are independently selected from S(═O)_(m), wherein each ring maybe substituted with up to 3 R^(a);

In an embodiment of the compounds of formula (I), A is CH and, whereinthe nitrogen of the pyrimidinium ring taken together with the contiguouslinking carbon atom and A as depicted in formula (I), form a four- toseven-membered ring, wherein such ring is not an aromatic ring, andwherein each remaining ring member is selected from carbon atoms and upto 3 heteroatoms independently selected from up to 2 O, up to 2 S, andup to 3 N(R^(c))_(p), wherein up to 2 carbon atom ring members areindependently selected from C(═O) and C(═S), and the sulfur atom ringmembers are independently selected from S(═O)_(m), wherein each ring maybe substituted with up to 3 R^(a);

In an embodiment of the compounds of formula (I), A is CH or N, andwherein the nitrogen of the pyrimidinium ring taken together with thecontiguous linking carbon atom and A as depicted in formula (I), form afive or six membered ring, wherein each remaining ring member isselected from carbon atoms and up to one heteroatoms independentlyselected from O, S, and N(R^(c))_(p), wherein each ring may besubstituted with up to one R^(a), wherein R^(a) has the meaning ashereunder described.

In an embodiment of the compounds of formula (I), A is CH or N, andwherein the nitrogen of the pyrimidinium ring taken together with thecontiguous linking carbon atom and A as depicted in formula (I), form afive or six membered ring, wherein such ring is not an aromatic ring,and wherein each remaining ring member is selected from carbon atoms andup to one heteroatoms independently selected from O, S, andN(R^(c))_(p), wherein each ring may be substituted with up to one R^(a),wherein R^(a) has the meaning as hereunder described.

In a further embodiment of the compounds of formula (I), A is CH or N,and wherein the nitrogen of the pyrimidinium ring taken together withthe contiguous linking carbon atom and A as depicted in formula (I),form a five membered ring, wherein each remaining ring member isselected from carbon atoms and up to one heteroatoms independentlyselected from O, S, and N(R^(c))_(p).

In a further embodiment of the compounds of formula (I), A is CH or N,and wherein the nitrogen of the pyrimidinium ring taken together withthe contiguous linking carbon atom and A as depicted in formula (I),form a five membered ring, wherein such ring is not an aromatic ring,and wherein each remaining ring member is selected from carbon atoms andup to one heteroatoms independently selected from O, S, andN(R^(c))_(p).

In a further embodiment of the compounds of formula (I), A is CH or N,and wherein the nitrogen of the pyrimidinium ring taken together withthe contiguous linking carbon atom and A as depicted in formula (I),form a six membered ring, wherein each remaining ring member is selectedfrom carbon atoms and up to one heteroatoms independently selected fromO, S, and N(R^(c))_(p).

In a further embodiment of the compounds of formula (I), A is CH or N,and wherein the nitrogen of the pyrimidinium ring taken together withthe contiguous linking carbon atom and A as depicted in formula (I),form a six membered ring, wherein such ring is not an aromatic ring, andwherein each remaining ring member is selected from carbon atoms and upto one heteroatoms independently selected from O, S, and N(R^(c))_(p).

In a further embodiment of the compounds of formula (I), A is CH, andwherein the nitrogen of the pyrimidinium ring taken together with thecontiguous linking carbon atom and A as depicted in formula (I), form afive membered ring, wherein each remaining ring member is selected fromcarbon atoms and up to one heteroatoms independently selected from O, S,and N(R^(c))_(p), wherein each ring may be substituted with up to oneR^(a), wherein R^(a) has the meaning as hereunder described.

In a further embodiment of the compounds of formula (I), A is CH, andwherein the nitrogen of the pyrimidinium ring taken together with thecontiguous linking carbon atom and A as depicted in formula (I), form afive membered ring, wherein such ring is not an aromatic ring, andwherein each remaining ring member is selected from carbon atoms and upto one heteroatoms independently selected from O, S, and N(R^(c))_(p),wherein each ring may be substituted with up to one R^(a), wherein R^(a)has the meaning as hereunder described.

In a further embodiment of the compounds of formula (I), A is CH, andwherein the nitrogen of the pyrimidinium ring taken together with thecontiguous linking carbon atom and A as depicted in formula (I), form afive membered ring, wherein each remaining ring member is selected fromcarbon atoms and up to one heteroatoms independently selected from O andS, wherein each ring may be substituted with up to one R^(a), whereinR^(a) has the meaning as hereunder described.

In a further embodiment of the compounds of formula (I), A is CH, andwherein the nitrogen of the pyrimidinium ring taken together with thecontiguous linking carbon atom and A as depicted in formula (I), form afive membered ring, wherein such ring is not an aromatic ring, andwherein each remaining ring member is selected from carbon atoms and upto one heteroatoms independently selected from O and S, wherein eachring may be substituted with up to one R^(a), wherein R^(a) has themeaning as hereunder described.

In a further embodiment of the compounds of formula (I), A is CH, andwherein the nitrogen of the pyrimidinium ring taken together with thecontiguous linking carbon atom and A as depicted in formula (I), form asix membered ring, wherein each remaining ring member is selected fromcarbon atoms and up to one heteroatoms independently selected from O, S,and N(R^(c))_(p), wherein each ring may be substituted with up to oneR^(a), wherein R^(a) has the meaning as hereunder described.

In a further embodiment of the compounds of formula (I), A is CH, andwherein the nitrogen of the pyrimidinium ring taken together with thecontiguous linking carbon atom and A as depicted in formula (I), form asix membered ring, wherein each remaining ring member is selected fromcarbon atoms and up to one heteroatoms independently selected from O, S,and N(R^(c))_(p), wherein each ring may be substituted with up to oneR^(a), wherein R^(a) has the meaning as hereunder described.

In a further embodiment of the compounds of formula (I), A is CH, andwherein the nitrogen of the pyrimidinium ring taken together with thecontiguous linking carbon atom and A as depicted in formula (I), form asix membered ring, wherein such ring is not an aromatic ring, andwherein each remaining ring member is selected from carbon atoms and upto one heteroatoms independently selected from O and S, wherein eachring may be substituted with up to one R^(a), wherein R^(a) has themeaning as hereunder described.

In a further embodiment, preferred are compounds of formula (I), whereinA is CH, and wherein the nitrogen of the pyrimidinium ring takentogether with the contiguous linking carbon atom and A as depicted informula (I), form a five or six membered ring resulting in the compoundsof formula (II) selected from the group of compounds of formulae II-1 toII-16

In a further embodiment, compounds of formula (I) are selected from thegroup of compounds of formulae II-1, II-2, II-3, II-4, II-5, II-6, II-8,II-9, II-10, II-11, II-12, II-13, II-14, II-15, and II-16.

In a further embodiment, compounds of formula (I) are selected from thegroup of compounds of formulae II-1, II-2, II-3, II-4, II-5, II-6, II-7and II-15.

In a further embodiment, compounds of formula (I) are selected from thegroup of compounds of formulae II-1, II-2, II-3, II-4, II-5, II-6 andII-7.

In a further embodiment, compounds of formula (I) are selected from thegroup of compounds of formulae II-1, II-2, II-3, II-4, II-5, II-6 andII-16.

In a further embodiment, compounds of formula (I) are selected from thegroup of compounds of formulae II-1, II-4, II-5, and II-6.

In a further embodiment, compounds of formula (I) are selected from thegroup of compounds of formulae, II-8, II-9, II-10, II-11, II-12, II-13,II-14, and II-15.

In a further embodiment, compounds of formula (I) are selected from thegroup of compounds of formulae, II-11, II-12, II-13, II-14, and II-15.

In a further embodiment, compounds of formula (I) are selected from thegroup of compounds of formulae, II-1, II-4, II-5, II-6, II-11, II-12,II-13, II-14, and II-15.

In a preferred embodiment, the compound of formula (I) is a compound offormula II-1. In an other embodiment, the compound of formula (I) is acompound of formula II-4.

In an other embodiment, the compound of formula (I) is a compound offormula II-5.

In an other embodiment, the compound of formula (I) is a compound offormula II-6.

In an other embodiment, the compound of formula (I) is a compound offormula II-11.

In an other embodiment, the compound of formula (I) is a compound offormula II-12.

In an other embodiment, the compound of formula (I) is a compound offormula II-13.

In an other embodiment, the compound of formula (I) is a compound offormula II-14.

In an other embodiment, the compound of formula (I) is a compound offormula II-15.

In an other embodiment, the compound of formula (I) is a compound offormula II-16.

In an embodiment, R¹ is hydrogen, C₁-C₈-alkyl, C₂-C₈-alkenyl,C₂-C₈-alkynyl, C₁-C₆-alkoxy, C₃-C₆-cycloalkyl, C₄-C₁₀-cycloalkenyl orC₅-C₁₁-cycloalkylcycloalkyl, wherein the C-atoms of the aforementionedgroups may be unsubstituted, or partially or fully substituted withR^(a), wherein R^(a) has the meaning as hereunder described.

In another embodiment, R¹ is a three- to ten-membered saturated, orpartially saturated or heterocyclic ring system, which may contain 1 to3 heteroatoms selected from N(R^(c))_(p), O, and S, wherein S may beoxidized and which heterocyclic ring may be unsubstituted or substitutedwith R^(a).

In a further embodiment, R¹ is hydrogen, C₁-C₄-alkyl, C₂-C₈-alkenyl,C₁-C₆-alkoxy, C₃-C₆-cycloalkyl or C₅-C₁₁-cycloalkylcycloalkyl, whereinthe C-atoms of the aforementioned groups may be unsubstituted, orpartially or fully substituted with halogen.

In a further embodiment R¹ is C₁-C₄-alkyl, C₂-C₈-alkenyl,C₃-C₆-cycloalkyl, phenyl or benzyl, wherein the C-atoms of theaforementioned groups may be unsubstituted, or partially or fullysubstituted with R^(a), wherein R^(a) has the meaning as hereunderdescribed.

In a further embodiment R¹ is C₁-C₄-alkyl, C₃-C₆-cycloalkyl or phenyl,wherein the C-atoms of the aforementioned groups may be unsubstituted,or partially or fully substituted with halogen or

In a further embodiment R¹ is C₁-C₄-alkyl, C₂-C₄-alkenyl, phenyl orbenzyl, wherein the c-atoms of the aforementioned groups may bepartially or fully substituted with halogen, preferably Cl or F.

In a further embodiment R¹ is C₁-C₄-alkyl, C₃-C₆-cycloalkyl or phenyl,preferably CH₃, CH₂CH₃, CH(CH₃)₂, cyclopropyl or phenyl.

In another embodiment R¹ is C₁-C₃-alkyl, preferably CH₃, CH₂CH₃ orCH(CH₃)₂; particularly R¹ is CH₂CH₃.

In an embodiment, R² is hydrogen, halogen, CN, NO₂, C₁-C₆ alkyl,C₁-C₆-haloalkyl, C₁-C₆-haloalkoxy, C₁-C₆-alkoxy, C₂-C₆-alkenyl,C₂-C₆-alkynyl, C₃-C₆-cycloalkyl, C₅-C₆-cycloalkenyl,C₅-C₁₄-cycloalkylcycloalkyl or S(O)_(m)R^(b), wherein the C-atoms of theaforementioned groups may be unsubstituted, or partially or fullysubstituted with R^(2a).

In an embodiment, R² is hydrogen, halogen, CN, C₁-C₆ alkyl,C₁-C₂-alkoxy-C₁-C₂-alkyl or C₃-C₆-cycloalkyl, wherein the C-atoms of theaforementioned groups may be substituted with halogen or CN.

In an embodiment, R² is hydrogen, halogen, CN or C₁-C₄-alkyl which maybe substituted with halogen.

In a further embodiment R² is CN.

In a further embodiment, R² is hydrogen or C₁-C₂-alkyl, particularlyCH₃.

In a further embodiment, R² is C₁-C₆-haloalkyl, preferablyC₁-C₂-haloalkyl, particularly halomethyl, such as CF₃ or CHF₂.

In another embodiment, R² is C₁-C₂-alkoxy-C₁-C₂-alkyl, preferablyC₁-C₂-alkoxy-methyl, particularly CH₂OCH₃.

In another embodiment, R² is C₃-C₆-cycloalkyl, preferably cyclopropylwhich may be substituted, preferably by halogen or cyano.

In another embodiment, R² is C₂-C₆-alkyl, preferably C₂-C₄-alkyl,particularly CH₂CH₃ or C(CH₃)₃.

In another embodiment, R² is C₁-C₆-alkyl, preferably C₁-C₂-alkyl,particularly CH₃.

In another embodiment, R² is halogen, preferably Cl or F, particularlyF.

In another embodiment, R² is a five- or six-membered carbo- orheterocyclic ring, which ring may be unsubstituted, partially, or fullysubstituted with R^(2a), and wherein R^(2a) is as hereunder defined orR^(2a) is preferably halogen, C₁-C₆-haloalkyl, C₁-C₆-haloalkoxy, OR^(c),C(═O)OR^(c), C(═O)NR^(b)R^(c), phenyl, or pyridyl which may besubstituted with halogen, C₁-C₆-haloalkyl or C₁-C₆-haloalkoxy. In afurther embodiment, R² is a six-membered carbo- or heterocyclic ring,which ring may be unsubstituted, partially, or fully substituted withR^(2a), and wherein R^(2a) is halogen, C₁-C₆-haloalkyl,C₁-C₆-haloalkoxy, OR^(c), C(═O)OR^(c), C(═O)NR^(b)R^(c), phenyl, orpyridyl which may be substituted with R^(2aa), wherein R^(2aa) is ashereunder defined.

In a further embodiment, R² is a six-membered aromatic carbocyclic ring,which ring may be unsubstituted, partially, or fully substituted withR^(2a), and wherein R^(2a) is halogen, C₁-C₆-haloalkyl,C₁-C₆-haloalkoxy, OR^(c), C(═O)OR^(c), C(═O)NR^(b)R^(c), phenyl, orpyridyl which may be substituted with R^(2aa), wherein R^(2aa) is ashereunder defined, preferably R^(2aa) is halogen, C₁-C₆-haloalkyl orC₁-C₆-haloalkoxy.

Within this embodiment, R² is phenyl which may be substituted withhalogen, C₁-C₆-haloalkyl or C₁-C₆-haloalkoxy.

Further, within this embodiment R² is phenyl which may be substitutedwith phenyl.

In a further embodiment, R² is a six-membered heterocyclic ring, whichcontains 1 or 2, preferably 1, heteroatom(s) selected from N—R^(c), O,and S, wherein S may be oxidised, which heterocyclic ring isunsubstituted or substituted with one or more groups R^(2a), whereinR^(2a) is as hereunder defined.

In an embodiment, R^(a) is halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl,C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₃-C₆-cycloalkyl, CN, OR^(c),NR^(b)R^(c), NO₂, phenyl, pyridyl, thiazyl, furanyl, pyrimidinyl orthienyl, wherein the C-atoms aforementioned which groups may beunsubstituted or substituted with one or more R^(aa), wherein R^(aa) isas hereunder defined.

In a further embodiment, R^(a) is halogen, C₁-C₄-alkyl, C₁-C₄-haloalkylor C₃-C₆-cycloalkyl.

In a further embodiment, R^(a) is halogen, C₁-C₄-alkyl, C₁-C₄-haloalkylor C₃-C₆-cycloalkyl.

In a further embodiment, R^(a) is halogen.

In an embodiment, R^(a) is halogen, CN, NO₂, S(O)_(m)R^(b), C(O)R^(c),C(O)OR^(c), C(O)NR^(b)R^(c), C(═S)NR^(b)R^(c), C₁-C₆-alkyl,C₃-C₆-cycloalkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-alkoxy,C₂-C₆-alkenyloxy or C₂-C₆-alkynyloxy, wherein the C-atoms of theaforementioned groups may be unsubstituted, partially or fullysubstituted with R^(aa), wherein is as hereunder defined.

In a further embodiment, R^(a) is halogen, CN, C₃-C₆-cycloalkyl,C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-alkoxy, C₂-C₆-alkenyloxy orC₂-C₆-alkynyloxy, which C-atoms of the aforementioned groups may beunsubstituted, partially or fully substituted with R^(aa), whereinR^(aa) is as hereunder defined.

In a further embodiment, R^(a) is halogen, CN, C₃-C₆-cycloalkyl,C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-alkoxy, C₂-C₆-alkenyloxy orC₂-C₆-alkynyloxy, wherein the C-atoms of the aforementioned groups maybe unsubstituted, partially or fully substituted with halogen.

In a further embodiment, R^(a) is halogen, C₁-C₆-haloalkyl orC₁-C₆-alkoxy.

In a further embodiment, R^(a) is halogen, CN or C₁-C₂-haloalkyl.

In a further embodiment, R^(a) is halogen or C₁-C₂-haloalkyl.

In an embodiment, R^(a) is halogen, preferably Br, Cl or F, particularlyCl.

In another embodiment, R^(a) is C₁-C₂-haloalkyl, preferably halomethylsuch as CHF₂ or CF₃, particularly CF₃.

In an embodiment, two geminally bound groups R^(a) together may form agroup selected from ═O, ═S, ═CR^(b)R^(c), ═NR^(c), ═NOR^(c), and═NNR^(c)R^(c);

In another embodiment, two geminally bound groups R^(a) together mayform a group selected from ═CR^(b)R^(c), ═NR^(c), ═NOR^(c), and═NNR^(c)R^(c);

In another embodiment, two geminally bound groups R^(a) together mayform a group selected from ═O, ═S and ═N(C₁-C₆-alkyl).

In another embodiment, two geminally bound groups R^(a) together mayform a ═N(C₁-C₆-alkyl) group.

In an embodiment, R^(b) is hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl,C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, phenyl, pyridyl, thiazyl or thienyl,wherein the C-atoms of the aforementioned groups may be substituted withR^(aa), wherein R^(aa) is as hereunder defined. In a further embodiment,R^(b) is hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy orC₁-C₆-haloalkoxy. In a further embodiment, R^(b) is hydrogen,C₁-C₆-alkyl or C₁-C₆-haloalkyl. In an embodiment, R^(b) is C₁-C₆-alkylor C₁-C₆-haloalkyl. In an embodiment, R^(b) is H.

In an embodiment, R^(c) is hydrogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl,C₁-C₄-alkylcarbonyl, C₁-C₆ cycloalkyl, phenyl, pyridyl, thiazyl orthienyl wherein the C-atoms of the aforementioned groups may besubstituted with R^(aa), wherein R^(aa) is as hereunder defined. In afurther embodiment, R^(c) is hydrogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl,C₁-C₄-alkylcarbonyl, or C₁-C₆-cycloalkyl. In an embodiment, R^(c) ishydrogen, C₁-C₆-alkyl or C₁-C₆-haloalkyl. In an embodiment, R^(c) isC₁-C₆-alkyl or C₁-C₆-haloalkyl. In an embodiment, R^(c) is H.

In an embodiment, two geminally bound groups R^(b)R^(b), R^(c)R^(b) orR^(c)R^(c) together with the atom to which they are bound, may form a3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated oraromatic carbo- or heterocyclic ring, which may contain 1 to 2heteroatoms or heteroatoms groups selected from N, O, S, NO, SO and SO₂and wherein the carbo- or heterocyclic ring may be partially or fullysubstituted with R⁴.

In another embodiment, two geminally bound groups R^(b)R^(b), R^(c)R^(b)or R^(c)R^(c) together with the atom to which they are bound, may form a5- or 6-membered saturated, partially unsaturated or aromaticcarbocyclic ring, which ring may be partially or fully substituted withR⁴, and wherein R⁴ is as hereunder defined.

In another embodiment, two geminally bound groups R^(b)R^(c), R^(c)R^(b)or R^(c)R^(c) together with the atom to which they are bound, may form a5- or 6-membered saturated, partially unsaturated or aromaticheterocyclic ring, which may contain 1 to 2 heteroatoms or heteroatomsgroups selected from N, O, S, NO, SO and SO₂, wherein the heterocyclicring may be partially or fully substituted with R⁴, and wherein R⁴ is ashereunder defined.

In an embodiment, R^(d) is hydrogen, phenyl, C₁-C₄-alkyl orC₂-C₆-alkenyl, wherein the aforementioned groups may be substituted withone or more halogen. In a further embodiment, R^(d) is C₁-C₄-alkyl orphenyl, which may be substituted with halogen. In another embodiment,R^(e) C₁-C₄-alkyl, preferably CH₃.

In an embodiment, R^(e) is C₁-C₄-alkyl, C₁-C₄-haloalkyl,C₁-C₄-alkylcarbonyl, C₁-C₆ cycloalkyl, phenyl, pyridyl, thiazyl orthienyl wherein the aforementioned groups may be substituted withR^(aa), wherein R^(aa) is as hereunder defined. In a further embodiment,R^(e) is C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkylcarbonyl, orC₁-C₆-cycloalkyl. In a further embodiment, R^(e) is C₁-C₄-alkyl orC₁-C₄-haloalkyl.

In an embodiment, R^(aa) is halogen, C₁-C₆-alkyl or C₁-C₆-haloalkyl. Inanother embodiment, R^(aa) is C₁-C₆-alkoxy or C₁-C₆-haloalkoxy. In anembodiment, R^(aa) is halogen.

In an embodiment, R^(2a) is halogen, C₁-C₆-haloalkyl, C₁-C₆-alkoxy,C₁-C₆-haloalkoxy, OR^(c), C(═O)OR^(c), C(═O)NR^(b)R^(c), or phenyl,wherein the C-atoms of the aforementioned groups may be unsubstituted orsubstituted with one or more R^(2aa), wherein R^(2aa) is as hereunderdefined, particularly R^(2a) is halogen, C₁-C₆-alkoxy, orC₁-C₆-haloalkoxy.

In an embodiment, two geminally bound groups R^(2a) together may form agroup selected from ═O, ═S and ═N(C₁-C₆-alkyl).

In an embodiment, R^(2a) is halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl,C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₃-C₆-cycloalkyl, CN, OR^(c),NR^(b)R^(c), NO₂, phenyl, pyridyl, thiazyl, furanyl, pyrimidinyl orthienyl, wherein the C-atoms of the aforementioned groups may beunsubstituted or substituted with one or more R^(2aa), wherein R^(2aa)is as hereunder defined.

In a further embodiment, R^(2a) is halogen, C₁-C₄-haloalkyl orC₃-C₆-haloalkoxy.

In a another embodiment, R^(2a) is phenyl which may be substituted withone or more R^(2aa).

In a another embodiment, R^(2a) is halogen. In another embodiment,R^(2a) is C₁-C₆-haloalkyl. In another embodiment, R^(2a) isC₁-C₆-haloalkoxy.

In another embodiment, R^(2a) is halogen, CN, NO₂, S(O)_(m)R^(b),C(═O)R^(c), C(═O)OR^(c), C(O)NR^(b)R^(c), C(═S)NR^(b)R^(c), C₁-C₆-alkyl,C₃-C₆-cycloalkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-alkoxy,C₂-C₆-alkenyloxy or C₂-C₆-alkynyloxy, which C-atoms of theaforementioned groups may be unsubstituted, partially or fullysubstituted with R^(aa), wherein is as hereunder defined.

In further embodiment, R^(2a) is, C(═O)OR^(c) or C(═O)NR^(b)R^(c).

In another embodiment, R^(2a) is halogen, CN, C₃-C₆-cycloalkyl,C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-alkoxy, C₂-C₆-alkenyloxy orC₂-C₆-alkynyloxy, which C-atoms of the aforementioned groups may beunsubstituted, partially or fully substituted with R^(2aa), whereinR^(2aa) is as hereunder defined.

In an embodiment, R^(2a) is Br, Cl or F, particularly Cl.

In another embodiment, R^(2a) is C₁-C₂-haloalkyl, preferably halomethylsuch as CHF₂ or CF₃, particularly CF₃.

In an embodiment, R^(2aa) is halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl,C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₂-C₄-alkenyl, C₂-C₄-alkynyl,C₃-C₆-cycloalkyl, CN, N(C₁-C₆-alkyl)(C(═O)(O)_(p)(C₁-C₆-alkyl),C(═O)N(C₁-C₆-alkyl)(S(O)_(m)(C₁-C₆-alkyl),SO₂N(C₁-C₆-alkyl)(C₁-C₆-alkyl), OSO₂(C₁-C₆-alkyl),N(C₁-C₆-alkyl)SO₂(C₁-C₆-alkyl), orS(═O)_(p)(═N(C₁-C₆-alkyl))(C₁-C₆-alkyl) or two geminally bound groupsR^(2aa) together may form a group selected from ═O, ═S and═N(C₁-C₆-alkyl).

In an embodiment, R^(2aa) is halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl,C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₂-C₄-alkenyl, C₂-C₄-alkynyl,C₃-C₆-cycloalkyl, CN, N(C₁-C₆-alkyl)(C(═O)(O)_(p)(C₁-C₆ alkyl),C(═O)N(C₁-C₆-alkyl)(S(O)_(m)(C₁-C₆-alkyl),SO₂N(C₁-C₆-alkyl)(C₁-C₆-alkyl), OSO₂(C₁-C₆-alkyl),N(C₁-C₆-alkyl)SO₂(C₁-C₆-alkyl), orS(═O)_(p)(═N(C₁-C₆-alkyl))(C₁-C₆-alkyl). In another embodiment, twogeminally bound groups R^(2aa) together may form a group selected from═O, ═S and ═N(C₁-C₆-alkyl).

In an embodiment, R⁴ is halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl,C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₂-C₄-alkenyl, C₂-C₄-alkynyl,C₃-C₆-cycloalkyl, CN, N(C₁-C₆-alkyl)(C(═O)(O)_(p)(C₁-C₆ alkyl),C(═O)N(C₁-C₆-alkyl)(S(O)_(m)(C₁-C₆-alkyl),SO₂N(C₁-C₆-alkyl)(C₁-C₆-alkyl), OSO₂(C₁-C₆-alkyl),N(C₁-C₆-alkyl)SO₂(C₁-C₆-alkyl), S(═O)_(p)(═N(C₁-C₆-alkyl))(C₁-C₆-alkyl),or two geminally bound groups R⁴ together may form a group selected from═O, ═S and ═N(C₁-C₆-alkyl).

In an embodiment, R⁴ is halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl,C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₂-C₄-alkenyl, C₂-C₄-alkynyl,C₃-C₆-cycloalkyl, CN, N(C₁-C₆-alkyl)(C(═O)(O)_(p)(C₁-C₆ alkyl),C(═O)N(C₁-C₆-alkyl)(S(O)_(m)(C₁-C₆-alkyl),SO₂N(C₁-C₆-alkyl)(C₁-C₆-alkyl), OSO₂(C₁-C₆-alkyl),N(C₁-C₆-alkyl)SO₂(C₁-C₆-alkyl), orS(═O)_(p)(═N(C₁-C₆-alkyl))(C₁-C₆-alkyl). In another embodiment, twogeminally bound groups R⁴ together may form a group selected from ═O, ═Sand ═N(C₁-C₆-alkyl).

In an embodiment, m is O. In another embodiment, m is 1. In anotherembodiment, m is 2.

In an embodiment, n is O. In another embodiment, n is 1. In anotherembodiment, n is 2.

In an embodiment, p is O. In another embodiment, p is 1.

In one embodiment, R³ is C₁-C₄-alkyl or C₁-C₄-haloalkyl, eachsubstituted with at least one substituent selected from cyano and NO₂,preferably C₁-C₄-alkyl substituted with at least one substituentselected from cyano and NO₂, preferably C₁-C₄-alkyl substituted with onecyano.

In a further embodiment, R³ is CH₂—CN or CH₂—CH₂—CN,

In a further embodiment, R³ is CH₂—CN.

In a further embodiment of compounds of formula (I), wherein

-   X, Y are each O;-   A is CH and the nitrogen of the pyrimidinium ring taken together    with the contiguous linking carbon atom and A as depicted in formula    (I), form a five or six membered ring, wherein each remaining ring    member is selected from 2 and 3 carbon atoms;-   R¹ is CH₃, CH₂CH₃, isopropyl, cyclopropyl, CH₂CF₃, phenyl, allyl or    benzyl;-   R² is phenyl which may be substituted with halogen, C₁-C₆-haloalkyl,    C₁-C₆-haloalkoxy or phenyl;-   Z is a direct bond and-   R³ is cyanoethyl or cyanomethyl.

In particular, with a view to their use, preference is given to thecompounds of the formula (I) compiled in the tables below, whichcompounds correspond to the compounds of formulae I.1.B (i.e. wherein Xand Y are O) and to the preferred compounds of formula II-1, II-2, II-3,II-4, II-5, II-6, II-7, and II-15. Each of the groups mentioned for thesubstituents in the tables are furthermore per se, independently of thecombination in which they are mentioned, a particularly preferred aspectof the substituent in question. Further, each individual meaning of asubstituent in the tables constitutes a particularly preferredembodiment of the substituents in question.

TABLE 1 Compounds of the formula (III-1) corresponding to the compoundsof the formula II-1, in which X and Y are O, R³ is cyanoethyl and thecombination of R¹, ZR² for a compound corresponds in each case to oneline of Table A:

III-1

TABLE 2 Compounds of the formula (III-2) corresponding to the compoundsof the formula II-2, in which X and Y are O, R³ is cyanoethyl, and thecombination of R¹, ZR² for a compound corresponds in each case to oneline of Table A:

III-2

TABLE 3 Compounds of the formula (III-3) corresponding to the compoundsof the formula II-3, in which X and Y are O, R³ is cyanoethyl, and thecombination of R¹, ZR² for a compound corresponds in each case to oneline of Table A.

III-3

TABLE 4 Compounds of the formula (III-4) corresponding to the compoundsof the formula II-4, in which X and Y are O, R³ is cyanoethyl, and thecombination of R¹, ZR² for a compound corresponds in each case to oneline of Table A.

III-4

TABLE 5 Compounds of the formula (III-5) corresponding to the compoundsof the formula II-5, in which X and Y are O, R³ is cyanoethyl, and thecombination of R¹, ZR² for a compound corresponds in each case to oneline of Table A.

III-5

TABLE 6 Compounds of the formula (III-6) corresponding to the compoundsof the formula II-6, in which X and Y are O, R³ is cyanoethyl, and thecombination of R¹, ZR² for a compound corresponds in each case to oneline of Table A.

III-6

TABLE 7 Compounds of the formula (III-7) corresponding to the compoundsof the formula II-7, in which X and Y are O, R³ is cyanoethyl, and thecombination of R¹, ZR² for a compound corresponds in each case to oneline of Table A.

III-7

TABLE 8 Compounds of the formula (III-8) corresponding to the compoundsof the formula II-15, in which X and Y are O, R³ is cyanoethyl, and thecombination of R¹, ZR² for a compound corresponds in each case to oneline of Table A.

III-8

TABLE 9 Compounds of the formula (III-9) corresponding to the compoundsof the formula II-1, in which X and Y are O, R³ is cyanomethyl, and thecombination of R¹, ZR² for a compound corresponds in each case to oneline of Table A:

III-9

TABLE 10 Compounds of the formula (III-10) corresponding to thecompounds of the formula II-2, in which X and Y are O, R³ iscyanomethyl, and the combination of R¹, ZR² for a compound correspondsin each case to one line of Table A:

III-9

TABLE 11 Compounds of the formula (III-11) corresponding to thecompounds of the formula II-3, in which X and Y are O, R³ iscyanomethyl, and the combination of R¹, ZR² for a compound correspondsin each case to one line of Table A.

III-11

TABLE 12 Compounds of the formula (III-12) corresponding to thecompounds of the formula II-4, in which X and Y are O, R³ iscyanomethyl, and the combination of R¹, ZR² for a compound correspondsin each case to one line of Table A.

III-12

TABLE 13 Compounds of the formula (III-13) corresponding to thecompounds of the formula II-5, in which X and Y are O, R³ iscyanomethyl, and the combination of R¹, ZR² for a compound correspondsin each case to one line of Table A.

III-13

TABLE 14 Compounds of the formula (III-14) corresponding to thecompounds of the formula II-6, in which X and Y are O, R³ iscyanomethyl, and the combination of R¹, ZR² for a compound correspondsin each case to one line of Table A.

III-14

TABLE 15 Compounds of the formula (III-15) corresponding to thecompounds of the formula II-7, in which X and Y are O, R³ iscyanomethyl, and the combination of R¹, ZR² for a compound correspondsin each case to one line of Table A.

III-15

TABLE 16 Compounds of the formula (III-16) corresponding to thecompounds of the formula II-15, in which X and Y are O, R³ iscyanomethyl, and the combination of R¹, ZR² for a compound correspondsin each case to one line of Table A.

III-16

TABLE 17 Compounds of the formula (III-17) corresponding to thecompounds of the formula II-1, in which X and Y are O, R³ is phenyl, andthe combination of R¹, ZR² for a compound corresponds in each case toone line of Table A:

III-17

TABLE 18 Compounds of the formula (III-18) corresponding to thecompounds of the formula II-2, in which X and Y are O, R³ is phenyl, andthe combination of R¹, ZR² for a compound corresponds in each case toone line of Table A:

III-18

TABLE 19 Compounds of the formula (III-19) corresponding to thecompounds of the formula II-3, in which X and Y are O, R³ is phenyl, andthe combination of R¹, ZR² for a compound corresponds in each case toone line of Table A.

III-19

TABLE 20 Compounds of the formula (III-20) corresponding to thecompounds of the formula II-4, in which X and Y are O, R³ is phenyl, andthe combination of R¹, ZR² for a compound corresponds in each case toone line of Table A.

III-20

TABLE 21 Compounds of the formula (III-21) corresponding to thecompounds of the formula II-5, in which X and Y are O, R³ is phenyl, andthe combination of R¹, ZR² for a compound corresponds in each case toone line of Table A.

III-21

TABLE 22 Compounds of the formula (III-22) corresponding to thecompounds of the formula II-6, in which X and Y are O, R³ is phenyl, andthe combination of R¹, ZR² for a compound corresponds in each case toone line of Table A.

III-22

TABLE 23 Compounds of the formula (III-23) corresponding to thecompounds of the formula II-7, in which X and Y are O, R³ is phenyl, andthe combination of R¹, ZR² for a compound corresponds in each case toone line of Table A. III-23

TABLE 24 Compounds of the formula (III-24) corresponding to thecompounds of the formula II-15, in which X and Y are O, R³ is phenyl,and the combination of R¹, ZR² for a compound corresponds in each caseto one line of Table A. III-24

TABLE 25 Compounds of the formula (III-25) corresponding to thecompounds of the formula II-1, in which X and Y are O, R³ isphenylmethyl and the combination of R¹, ZR² for a compound correspondsin each case to one line of Table A: III-25

TABLE 26 Compounds of the formula (III-26) corresponding to thecompounds of the formula II-2, in which X and Y are O, R³ isphenylmethyl, and the combination of R¹, ZR² for a compound correspondsin each case to one line of Table A: III-26

TABLE 27 Compounds of the formula (III-27) corresponding to thecompounds of the formula II-3, in which X and Y are O, R³ isphenylmethyl, and the combination of R¹, ZR² for a compound correspondsin each case to one line of Table A. III-27

TABLE 28 Compounds of the formula (III-28) corresponding to thecompounds of the formula II-4, in which X and Y are O, R³ isphenylmethyl, and the combination of R¹, ZR² for a compound correspondsin each case to one line of Table A. III-28

TABLE 29 Compounds of the formula (III-29) corresponding to thecompounds of the formula II-5, in which X and Y are O, R³ isphenylmethyl, and the combination of R¹, ZR² for a compound correspondsin each case to one line of Table A. III-29

TABLE 30 Compounds of the formula (III-30) corresponding to thecompounds of the formula II-6, in which X and Y are O, R³ isphenylmethyl, and the combination of R¹, ZR² for a compound correspondsin each case to one line of Table A. III-30

TABLE 31 Compounds of the formula (III-31) corresponding to thecompounds of the formula II-7, in which X and Y are O, R³ isphenylmethyl, and the combination of R¹, ZR² for a compound correspondsin each case to one line of Table A. III-31

TABLE 32 Compounds of the formula (III-32) corresponding to thecompounds of the formula II-15, in which X and Y are O, R³ isphenylmethyl, and the combination of R¹, ZR² for a compound correspondsin each case to one line of Table A. III-32

TABLE 33 Compounds of the formula (III-33) corresponding to thecompounds of the formula II-17, in which X and Y are O, R³ iscyanoethyl, and the combination of R¹, ZR² for a compound corresponds ineach caseto one line of Table A. III-33

TABLE 34 Compounds of the formula (III-34) corresponding to thecompounds of the formula II-17, in which X and Y are O, R³ iscyanomethyl, and the combination of R¹, ZR² for a compound correspondsin each case to one line of Table A. III-34

TABLE 35 Compounds of the formula (III-35) corresponding to thecompounds of the formula II-17, in which X and Y are O, R³ is phenyl,and the combination of R¹, ZR² for a compound corresponds in each caseto one line of Table A. III-35

TABLE 36 Compounds of the formula (III-36) corresponding to thecompounds of the formula II-17, in which X and Y are O, R³ isphenylmethyl, and the combination of R¹, ZR² for a compound correspondsin each case to one line of Table A. III-36

TABLE A No. ZR² R¹ A-1 C₆H₅ CH₃ A-2 2-fluorophenyl CH₃ A-32-methoxyphenyl CH₃ A-4 2,4-difluorophenyl CH₃ A-5 2,6-difluorophenylCH₃ A-6 4-fluorophenyl CH₃ A-7 CO₂CH₂CH₃ CH₃ A-8 C(O)CF₃ CH₃ A-9C(O)C₆H₅ CH₃ A-10 3-methoxyphenyl CH₃ A-11 3-cyanophenyl CH₃ A-123-(CO₂CH₂CH₃)phenyl CH₃ A-13 3-(C(O)N(CH₃)₂)phenyl CH₃ A-143-(trifluoromethyl)phenyl CH₃ A-15 3-(trifluoromethoxy)phenyl CH₃ A-163,5-dichlorophenyl CH₃ A-17 3-fluoro-5-methylphenyl CH₃ A-182-methoxy-5(trifluoromethyl)phenyl CH₃ A-193-chloro-5(trifluoromethyl)phenyl CH₃ A-203-(2-chloro-4-(trifluoromethyl)phenyl)phenyl CH₃ A-213-(2-chloro-4-(trifluoromethyl)phenyl)-4- CH₃ fluorophenyl A-223-(2-chloro-4-(trifluoromethyl)phenyl)-5- CH₃ methylphenyl A-233-phenylphenyl CH₃ A-24 4-methoxyphenyl CH₃ A-253-(3-chloro-5-trifluoromethyl-pyridine-2- CH₃ yl)phenyl A-26 C₆H₅ CH₂CH₃A-27 2-fluorophenyl CH₂CH₃ A-28 2-methoxyphenyl CH₂CH₃ A-292,4-difluorophenyl CH₂CH₃ A-30 2,6-difluorophenyl CH₂CH₃ A-314-fluorophenyl CH₂CH₃ A-32 CO₂CH₂CH₃ CH₂CH₃ A-33 C(O)CF₃ CH₂CH₃ A-34C(O)C₆H₅ CH₂CH₃ A-35 3-methoxyphenyl CH₂CH₃ A-36 3-cyanophenyl CH₂CH₃A-37 3-(CO₂CH₂CH₃)phenyl CH₂CH₃ A-38 3-(C(O)N(CH₃)₂)phenyl CH₂CH₃ A-393-(trifluoromethyl)phenyl CH₂CH₃ A-40 3-(trifluoromethoxy)phenyl CH₂CH₃A-41 3,5-dichlorophenyl CH₂CH₃ A-42 3-fluoro-5-methylphenyl CH₂CH₃ A-432-methoxy-5(trifluoromethyl)phenyl CH₂CH₃ A-443-chloro-5(trifluoromethyl)phenyl CH₂CH₃ A-453-(2-chloro-4-(trifluoromethyl)phenyl)phenyl CH₂CH₃ A-463-(2-chloro-4-(trifluoromethyl)phenyl)-4- CH₂CH₃ fluorophenyl A-473-(2-chloro-4-(trifluoromethyl)phenyl)-5- CH₂CH₃ methylphenyl A-483-phenylphenyl CH₂CH₃ A-49 4-methoxyphenyl CH₂CH₃ A-503-(3-chloro-5-trifluoromethyl-pyridine-2-yl- CH₂CH₃ phenyl A-51 C₆H₅CH(CH₃)₂ A-52 2-fluorophenyl CH(CH₃)₂ A-53 2-methoxyphenyl CH(CH₃)₂ A-542,4-difluorophenyl CH(CH₃)₂ A-55 2,6-difluorophenyl CH(CH₃)₂ A-564-fluorophenyl CH(CH₃)₂ A-57 CO₂CH₂CH₃ CH(CH₃)₂ A-58 C(O)CF₃ CH(CH₃)₂A-59 C(O)C₆H₅ CH(CH₃)₂ A-60 3-methoxyphenyl CH(CH₃)₂ A-61 3-cyanophenylCH(CH₃)₂ A-62 3-(CO₂CH₂CH₃)phenyl CH(CH₃)₂ A-63 3-(C(O)N(CH₃)₂)phenylCH(CH₃)₂ A-64 3-(trifluoromethyl)phenyl CH(CH₃)₂ A-653-(trifluoromethoxy)phenyl CH(CH₃)₂ A-66 3,5-dichlorophenyl CH(CH₃)₂A-67 3-fluoro-5-methylphenyl CH(CH₃)₂ A-682-methoxy-5(trifluoromethyl)phenyl CH(CH₃)₂ A-693-chloro-5(trifluoromethyl)phenyl CH(CH₃)₂ A-703-(2-chloro-4-(trifluoromethyl)phenyl)phenyl CH(CH₃)₂ A-713-(2-chloro-4-(trifluoromethyl)phenyl)-4- CH(CH₃)₂ fluorophenyl A-723-(2-chloro-4-(trifluoromethyl)phenyl)-5- CH(CH₃)₂ methylphenyl A-733-phenylphenyl CH(CH₃)₂ A-74 4-methoxyphenyl CH(CH₃)₂ A-753-(3-chloro-5-trifluoromethyl-pyridine-2-yl- CH(CH₃)₂ phenyl A-76 C₆H₅CH₂CH═CH₂ A-77 2-fluorophenyl CH₂CH═CH₂ A-78 2-methoxyphenyl CH₂CH═CH₂A-79 2,4-difluorophenyl CH₂CH═CH₂ A-80 2,6-difluorophenyl CH₂CH═CH₂ A-814-fluorophenyl CH₂CH═CH₂ A-82 CO₂CH₂CH₃ CH₂CH═CH₂ A-83 C(O)CF₃ CH₂CH═CH₂A-84 C(O)C₆H₅ CH₂CH═CH₂ A-85 3-methoxyphenyl CH₂CH═CH₂ A-863-cyanophenyl CH₂CH═CH₂ A-87 3-(CO₂CH₂CH₃)phenyl CH₂CH═CH₂ A-883-(C(O)N(CH₃)₂)phenyl CH₂CH═CH₂ A-89 3-(trifluoromethyl)phenyl CH₂CH═CH₂A-90 3-(trifluoromethoxy)phenyl CH₂CH═CH₂ A-91 3,5-dichlorophenylCH₂CH═CH₂ A-92 3-fluoro-5-methylphenyl CH₂CH═CH₂ A-932-methoxy-5(trifluoromethyl)phenyl CH₂CH═CH₂ A-943-chloro-5(trifluoromethyl)phenyl CH₂CH═CH₂ A-953-(2-chloro-4-(trifluoromethyl)phenyl)phenyl CH₂CH═CH₂ A-963-(2-chloro-4-(trifluoromethyl)phenyl)-4- CH₂CH═CH₂ fluorophenyl A-973-(2-chloro-4-(trifluoromethyl)phenyl)-5- CH₂CH═CH₂ methylphenyl A-983-phenylphenyl CH₂CH═CH₂ A-99 4-methoxyphenyl CH₂CH═CH₂ A-1003-(3-chloro-5-trifluoromethyl-pyridine-2- CH₂CH═CH₂ yl)phenyl A-101 C₆H₅CH₂C₆H₅ A-102 2-fluorophenyl CH₂C₆H₅ A-103 2-methoxyphenyl CH₂C₆H₅ A-1042,4-difluorophenyl CH₂C₆H₅ A-105 2,6-difluorophenyl CH₂C₆H₅ A-1064-fluorophenyl CH₂C₆H₅ A-107 CO₂CH₂CH₃ CH₂C₆H₅ A-108 C(O)CF₃ CH₂C₆H₅A-109 C(O)C₆H₅ CH₂C₆H₅ A-110 3-methoxyphenyl CH₂C₆H₅ A-111 3-cyanophenylCH₂C₆H₅ A-112 3-(CO₂CH₂CH₃)phenyl CH₂C₆H₅ A-113 3-(C(O)N(CH₃)₂)phenylCH₂C₆H₅ A-114 3-(trifluoromethyl)phenyl CH₂C₆H₅ A-1153-(trifluoromethoxy)phenyl CH₂C₆H₅ A-116 3,5-dichlorophenyl CH₂C₆H₅A-117 3-fluoro-5-methylphenyl CH₂C₆H₅ A-1182-methoxy-5(trifluoromethyl)phenyl CH₂C₆H₅ A-1193-chloro-5(trifluoromethyl)phenyl CH₂C₆H₅ A-1203-(2-chloro-4-(trifluoromethyl)phenyl)phenyl CH₂C₆H₅ A-1213-(2-chloro-4-(trifluoromethyl)phenyl)-4- CH₂C₆H₅ fluorophenyl A-1223-(2-chloro-4-(trifluoromethyl)phenyl)-5- CH₂C₆H₅ methylphenyl A-1233-phenylphenyl CH₂C₆H₅ A-124 4-methoxyphenyl CH₂C₆H₅ A-1253-(3-chloro-5-trifluoromethyl-pyridine-2- CH₂C₆H₅ yl)phenyl A-126 C₆H₅CH₂CF₃ A-127 2-fluorophenyl CH₂CF₃ A-128 2-methoxyphenyl CH₂CF₃ A-1292,4-difluorophenyl CH₂CF₃ A-130 2,6-difluorophenyl CH₂CF₃ A-1314-fluorophenyl CH₂CF₃ A-132 CO₂CH₂CH₃ CH₂CF₃ A-133 C(O)CF₃ CH₂CF₃ A-134C(O)C₆H₅ CH₂CF₃ A-135 3-methoxyphenyl CH₂CF₃ A-136 3-cyanophenyl CH₂CF₃A-137 3-(CO₂CH₂CH₃)phenyl CH₂CF₃ A-138 3-(C(O)N(CH₃)₂)phenyl CH₂CF₃A-139 3-(trifluoromethyl)phenyl CH₂CF₃ A-140 3-(trifluoromethoxy)phenylCH₂CF₃ A-141 3,5-dichlorophenyl CH₂CF₃ A-142 3-fluoro-5-methylphenylCH₂CF₃ A-143 2-methoxy-5(trifluoromethyl)phenyl CH₂CF₃ A-1443-chloro-5(trifluoromethyl)phenyl CH₂CF₃ A-1453-(2-chloro-4-(trifluoromethyl)phenyl)phenyl CH₂CF₃ A-1463-(2-chloro-4-(trifluoromethyl)phenyl)-4- CH₂CF₃ fluorophenyl A-1473-(2-chloro-4-(trifluoromethyl)phenyl)-5- CH₂CF₃ methylphenyl A-1483-phenylphenyl CH₂CF₃ A-149 4-methoxyphenyl CH₂CF₃ A-1503-(3-chloro-5-trifluoromethyl-pyridine-2- CH₂CF₃ yl)phenyl

The compound of formula (I) according to the present invention can beprepared according to the following syntheses routes, e.g. according tothe preparation methods and preparation schemes as described below.

The compound of formula (I) according to the present invention can beprepared. according to the e.g. preparation methods and preparationschemes as described below.

The compounds used as starting materials for the syntheses of thecompounds according to the present invention can generally be preparedby standard methods of organic chemistry. If not otherwise specified,the definitions of the variables such as X, Y, R³, R¹ and R² of thestructures given in the schemes have the same meaning as defined above.

Compounds of the formula (I) can for example be prepared by reacting theappropriately substituted compounds P-1 with the a malonate derivativeP-2 analogous to the methods described by Holyoke et al. in WO2009/099929 (Scheme 1):

Compounds like P-1 can be prepared from the corresponding compounds P-3,by reacting it with an amine nucleophile like P-4 as described by, forexample, Michel Langlois et al, Journal of Heterocyclic Chemistry,19(1), 193-200; 1982, wherein LG denotes a leaving group such as halogen(e.g. chlorine or bromine), OR′, or SR′, with R′ being C₁-C₆-alkyl,preferably chlorine methoxy ethoxy, methylthio or ethylthio (Scheme 2):

Compounds like P-3 are available from the corresponding lactams P-5 bystandard procedures known to a person skilled in the art. For examplesee Allen, Jennifer Rebecca et al in WO 2004/094382 or Lang, Kai et al,Journal of Organic Chemistry, 75(19), 6424-6435; 2010 (Scheme 3):

Lactams are widespread in organic chemistry and methods to produce themare well known. For example see: Smith, M. B. in Science of Synthesis,(2005) 21, 653.

If individual compounds cannot be prepared via the above describedroutes, they can be prepared by derivatization of other compounds offormula (I) or by customary modifications of the synthesis routesdescribed.

For example, in individual cases, certain compounds of formula (I) canadvantageously be prepared from other compounds of formula (I) byderivatization, e.g. by ester hydrolysis, amidation, esterification,ether cleavage, olefination, reduction, oxidation and the like, or bycustomary modifications of the synthesis routes described.

The reaction mixtures are worked up in the customary manner, for exampleby mixing with water, separating the phases, and, if appropriate,purifying the crude products by chromatography, for example on aluminaor silica gel.

As used herein, the term “compound(s) of the present invention” or“compound(s) according to the invention” refers to the compound(s) offormula (I) as defined above, which are also referred to as “compound(s)of formula I” or “compound(s) I” or “formula I compound(s)”, andincludes their salts, tautomers, stereoisomers, and N-oxides.

Mixtures

The present invention also relates to a mixture of at least one compoundof the present invention with at least one mixing partner as definedherein after. Preferred are binary mixtures of one compound of thepresent invention as component I with one mixing partner as definedherein after as component II. Preferred weight ratios for such binarymixtures are from 5000:1 to 1:5000, preferably from 1000:1 to 1:1000,more preferably from 100:1 to 1:100, particularly preferably from 10:1to 1:10. In such binary mixtures, components I and II may be used inequal amounts, or an excess of component I, or an excess of component IImay be used.

Mixing partners can be selected from pesticides, in particularinsecticides, nematicides, and acaricides, fungicides, herbicides, plantgrowth regulators, fertilizers, and the like. Preferred mixing partnersare insecticides, nematicides and fungicides.

The following list M of pesticides, grouped and numbered according theMode of Action Classification of the Insecticide Resistance ActionCommittee (IRAC), together with which the compounds of the presentinvention can be used and with which potential synergistic effects mightbe produced, is intended to illustrate the possible combinations, butnot to impose any limitation:

M.1 Acetylcholine esterase (AChE) inhibitors from the class of: M.1Acarbamates, for example aldicarb, alanycarb, bendiocarb, benfuracarb,butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan,ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb,methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur,thiodicarb, thiofanox, trimethacarb, XMC, xylylcarb and triazamate; orfrom the class of M.1B organophosphates, for example acephate,azamethiphos, azinphos-ethyl, azinphosmethyl, cadusafos, chlorethoxyfos,chlorfenvinphos, chlormephos, chlorpyrifos, chlorpyrifos-methyl,coumaphos, cyanophos, demeton-S-methyl, diazinon, dichlorvos/DDVP,dicrotophos, dimethoate, dimethylvinphos, disulfoton, EPN, ethion,ethoprophos, famphur, fenamiphos, fenitrothion, fenthion, fosthiazate,heptenophos, imicyafos, isofenphos, isopropylO-(methoxyaminothio-phosphoryl) salicylate, isoxathion, malathion,mecarbam, methamidophos, methidathion, mevinphos, monocrotophos, naled,omethoate, oxydemeton-methyl, parathion, parathion-methyl, phenthoate,phorate, phosalone, phosmet, phosphamidon, phoxim, pirimiphos-methyl,profenofos, propetamphos, prothiofos, pyraclofos, pyridaphenthion,quinalphos, sulfotep, tebupirimfos, temephos, terbufos,tetrachlorvinphos, thiometon, triazophos, trichlorfon and vamidothion;

M.2. GABA-gated chloride channel antagonists such as: M.2A cyclodieneorganochlorine compounds, as for example endosulfan or chlordane; orM.2B fiproles (phenylpyrazoles), as for example ethiprole, fipronil,flufiprole, pyrafluprole and pyriprole;

M.3 Sodium channel modulators from the class of M.3A pyrethroids, forexample acrinathrin, allethrin, d-cis-trans allethrin, d-transallethrin, bifenthrin, bioallethrin, bioallethrin S-cylclopentenyl,bioresmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin,lambda-cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha-cypermethrin,beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, cyphenothrin,deltamethrin, empenthrin, esfenvalerate, etofenprox, fenpropathrin,fenvalerate, flucythrinate, flumethrin, tau-fluvalinate, halfenprox,heptafluthrin, imiprothrin, meperfluthrin,metofluthrin, momfluorothrin,permethrin, phenothrin, prallethrin, profluthrin, pyrethrin (pyrethrum),resmethrin, silafluofen, tefluthrin, tetramethylfluthrin, tetramethrin,tralomethrin and transfluthrin; or M.3B sodium channel modulators suchas DDT or methoxychlor;

M.4 Nicotinic acetylcholine receptor agonists (nAChR) from the class ofM.4A neonicotinoids, for example acetamiprid, clothianidin, cycloxaprid,dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam; orthe compounds M.4A.2:(2E-)-1-[(6-Chloropyridin-3-yl)methyl]-N′-nitro-2-pentylidenehydrazinecarboximidamide;or M4.A.3:1-[(6-Chloropyridin-3-yl)methyl]-7-methyl-8-nitro-5-propoxy-1,2,3,5,6,7-hexahydroimidazo[1,2-a]pyridine;or from the class M.4B nicotine;

M.5 Nicotinic acetylcholine receptor allosteric activators from theclass of spinosyns, for example spinosad or spinetoram;

M.6 Chloride channel activators from the class of avermectins andmilbemycins, for example abamectin, emamectin benzoate, ivermectin,lepimectin or milbemectin;

M.7 Juvenile hormone mimics, such as M.7A juvenile hormone analogues ashydroprene, kinoprene and methoprene; or others as M.78 fenoxycarb orM.7C pyriproxyfen;

M.8 miscellaneous non-specific (multi-site) inhibitors, for example M.8Aalkyl halides as methyl bromide and other alkyl halides, or M.88chloropicrin, or M.8C sulfuryl fluoride, or M.8D borax, or M.8E tartaremetic;

M.9 Selective homopteran feeding blockers, for example M.98 pymetrozine,or M.9C flonicamid;

M.10 Mite growth inhibitors, for example M.10A clofentezine, hexythiazoxand diflovidazin, or M.10B etoxazole;

M.11 Microbial disruptors of insect midgut membranes, for exampleBacillus thuringiensis or Bacillus sphaericus and the insecticdalproteins they produce such as Bacillus thuringiensis subsp. israelensis,Bacillus sphaericus, Bacillus thuringiensis subsp. aizawai, Bacillusthuringiensis subsp. kurstaki and Bacillus thuringiensis subsp.tenebrionis, or the Bt crop proteins: Cry1Ab, Cry1Ac, Cry1Fa, Cry2Ab,mCry3A, Cry3Ab, Cry3Bb and Cry34/35Ab1;

M.12 Inhibitors of mitochondrial ATP synthase, for example M.12Adiafenthiuron, or M.12B organotin miticides such as azocyclotin,cyhexatin or fenbutatin oxide, or M.12C propargite, or M.12D tetradifon;

M.13 Uncouplers of oxidative phosphorylation via disruption of theproton gradient, for example chlorfenapyr, DNOC or sulfluramid;

M.14 Nicotinic acetylcholine receptor (nAChR) channel blockers, forexample nereistoxin analogues as bensultap, cartap hydrochloride,thiocyclam or thiosultap sodium;

M.15 Inhibitors of the chitin biosynthesis type 0, such as benzoylureasas for example bistrifluron, chlorfluazuron, diflubenzuron,flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron,noviflumuron, teflubenzuron or triflumuron;

M.16 Inhibitors of the chitin biosynthesis type 1, as for examplebuprofezin;

M.17 Moulting disruptors, Dipteran, as for example cyromazine;

M.18 Ecdyson receptor agonists such as diacylhydrazines, for examplemethoxyfenozide, tebufenozide, halofenozide, fufenozide orchromafenozide;

M.19 Octopamin receptor agonists, as for example amitraz;

M.20 Mitochondrial complex III electron transport inhibitors, forexample M.20A hydramethylnon, or M.206 acequinocyl, or M.20Cfluacrypyrim;

M.21 Mitochondrial complex I electron transport inhibitors, for exampleM.21A METI acaricides and insecticides such as fenazaquin,fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad or tolfenpyrad, orM.216 rotenone;

M.22 Voltage-dependent sodium channel blockers, for example M.22Aindoxacarb, or M.22B metaflumizone, or M.22B.1:2-[2-(4-Cyanophenyl)-1-[3-(trifluoromethyl)phenyl]ethylidene]-N-[4-(difluoromethoxy)phenyl]-hydrazinecarboxamideor M.22B.2:N-(3-Chloro-2-methylphenyl)-2-[(4-chlorophenyl)[4-[methyl(methylsulfonyl)amino]phenyl]methylene]-hydrazinecarboxamide;

M.23 Inhibitors of the of acetyl CoA carboxylase, such as Tetronic andTetramic acid derivatives, for example spirodiclofen, spiromesifen orspirotetramat;

M.24 Mitochondrial complex IV electron transport inhibitors, for exampleM.24A phosphine such as aluminium phosphide, calcium phosphide,phosphine or zinc phosphide, or M.246 cyanide;

M.25 Mitochondrial complex II electron transport inhibitors, such asbeta-ketonitrile derivatives, for example cyenopyrafen or cyflumetofen;

M.28 Ryanodine receptor-modulators from the class of diamides, as forexample flubendiamide, chlorantraniliprole (Rynaxypyr®),cyantraniliprole (Cyazypyr®), tetraniliprole, or the phthalamidecompounds M.28.1: (R)-3-Chlor-N1-{2-methyl-4-[1,2,2,2tetrafluor-1-(trifluormethyl)ethyl]phenyl}-N2-(1-methyl-2-methylsulfonylethyl)phthalamidand M.28.2: (S)-3-Chlor-N1-{2-methyl-4-[1,2,2,2tetrafluor-1-(trifluormethyl)ethyl]phenyl}-N2-(1-methyl-2-methylsulfonylethyl)phthalamid,or the compound M.28.3:3-bromo-N-{2-bromo-4-chloro-6-[(1-cyclopropylethyl)carbamoyl]phenyl}-1-(3-chlorpyridin-2-yl)-1H-pyrazole-5-carboxamide(proposed ISO name: cyclaniliprole), or the compound M.28.4:methyl-2-[3,5-dibromo-2-({[3-bromo-1-(3-chlorpyridin-2-yl)-1H-pyrazol-5-yl]carbonyl}amino)benzoyl]-1,2-dimethylhydrazinecarbovlate;or a compound selected from M.28.5a) to M.28.5d) and M.28.5h) toM.28.5I): M.28.5a)N-[4,6-dichloro-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide;M.28.5b)N-[4-chloro-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]-6-methyl-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide;M.28.5c)N-[4-chloro-2-[(di-2-propyl-lambda-4-sulfanylidene)carbamoyl]-6-methyl-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide;M.28.5d)N-[4,6-dichloro-2-[(di-2-propyl-lambda-4-sulfanylidene)carbamoyl]-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide;M.28.5h)N-[4,6-dibromo-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide;M.28.5i)N-[2-(5-Amino-1,3,4-thiadiazol-2-yl)-4-chloro-6-methylphenyl]-3-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxamide;M.28.5j)3-Chloro-1-(3-chloro-2-pyridinyl)-N-[2,4-dichloro-6-[[(1-cyano-1-methylethyl)amino]carbonyl]phenyl]-1H-pyrazole-5-carboxamide;M.28.5k)3-Bromo-N-[2,4-dichloro-6-(methylcarbamoyl)phenyl]-1-(3,5-dichloro-2-pyridyl)-1H-pyrazole-5-carboxamide;M.28.51)N-[4-Chloro-2-[[(1,1-dimethylethyl)amino]carbonyl]-6-methylphenyl]-1-(3-chloro-2-pyridinyl)-3-(fluoromethoxy)-1H-pyrazole-5-carboxamide;or

M.28.6: cyhalodiamide; or;

M.29. insecticidal active compounds of unknown or uncertain mode ofaction, as for example afidopyropen, afoxolaner, azadirachtin,amidoflumet, benzoximate, bifenazate, broflanilide, bromopropylate,chinomethionat, cryolite, dicloromezotiaz, dicofol, flufenerim,flometoquin, fluensulfone, fluhexafon, fluopyram, flupyradifurone,fluralaner, metoxadiazone, piperonyl butoxide, pyflubumide, pyridalyl,pyrifluquinazon, sulfoxaflor, tioxazafen, triflumezopyrim, or thecompounds

M.29.3:11-(4-chloro-2,6-dimethylphenyl)-12-hydroxy-1,4-dioxa-9-azadispiro[4.2.4.2]-tetradec-11-en-10-one,or the compound

M.29.4:3-(4′-fluoro-2,4-dimethylbiphenyl-3-yl)-4-hydroxy-8-oxa-1-azaspiro[4.5]dec-3-en-2-one,or the compound

M.29.5:1-[2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl]-3-(trifluoromethyl)-1H-1,2,4-triazole-5-amine,or actives on basis of Bacillus firmus (Votivo, 1-1582); or

a compound selected from the group of M.29.6, wherein the compound isselected from M.29.6a) to M.29.6k): M.29.6a)(E/Z)-N-[1-[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2,2-trifluoro-acetamide;M.29.6b)(E/Z)-N-[1-[(6-chloro-5-fluoro-3-pyridyl)methyl]-2-pyridylidene]-2,2,2-trifluoro-acetamide;M.29.6c)(E/Z)-2,2,2-trifluoro-N-[1-[(6-fluoro-3-pyridyl)methyl]-2-pyridylidene]acetamide;M.29.6d)(E/Z)-N-[1-[(6-bromo-3-pyridyl)methyl]-2-pyridylidene]-2,2,2-trifluoro-acetamide;M.29.6e)(E/Z)-N-[1-[1-(6-chloro-3-pyridyl)ethyl]-2-pyridylidene]-2,2,2-trifluoro-acetamide;M.29.6f)(E/Z)-N-[1-[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2-difluoro-acetamide;M.29.6g)(E/Z)-2-chloro-N-[1-[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2-difluoro-acetamide;M.29.6h)(E/Z)-N-[1-[(2-chloropyrimidin-5-yl)methyl]-2-pyridylidene]-2,2,2-trifluoro-acetamide;M.29.6i)(E/Z)-N-[1-[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2,3,3,3-pentafluoro-propanamide);M.29.6j)N-[1-[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2,2-trifluoro-thioacetamide;or M.29.6k)N-[1-[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2,2-trifluoro-N′-isopropyl-acetamidine;or the compounds

M.29.8: fluazaindolizine; or the compounds

M.29.9.a):4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-2-methyl-N-(1-oxothietan-3-yl)benzamide;or M.29.9.b): fluxametamide; or

M.29.10:5-[3-[2,6-dichloro-4-(3,3-dichloroallyloxy)phenoxy]propoxy]-1H-pyrazole;or

a compound selected from the group of M.29.11, wherein the compound isselected from M.29.11b) to M.29.11p): M.29.11.b)3-(benzoylmethylamino)-N-[2-bromo-4-[1,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]-6-(trifluoromethyl)phenyl]-2-fluoro-benzamide;M.29.11.c)3-(benzoylmethylamino)-2-fluoro-N-[2-iodo-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]-6-(trifluoromethyl)phenyl]-benzamide;M.29.11.d)N-[3-[[[2-iodo-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]-6-(trifluoromethyl)phenyl]amino]carbonyl]phenyl]-N-methyl-benzamide;M.29.11.e)N-[3-[[[2-bromo-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]-6-(trifluoromethyl)phenyl]amino]carbonyl]-2-fluorophenyl]-4-fluoro-N-methyl-benzamide;M.29.11.f)4-fluoro-N-[2-fluoro-3-[[[2-iodo-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]-6-(trifluoromethyl)phenyl]amino]carbonyl]phenyl]-N-methyl-benzamide;M.29.11.g)3-fluoro-N-[2-fluoro-3-[[[2-iodo-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]-6-(trifluoromethyl)phenyl]amino]carbonyl]phenyl]-N-methyl-benzamide;M.29.11.h)2-chloro-N-[3-[[[2-iodo-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]-6-(trifluoromethyl)phenyl]amino]carbonyl]phenyl]-3-pyridinecarboxamide;M.29.11.i)4-cyano-N-[2-cyano-5-[[2,6-dibromo-4-[1,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]phenyl]carbamoyl]phenyl]-2-methyl-benzamide;M.29.11j)4-cyano-3-[(4-cyano-2-methyl-benzoyl)amino]-N-[2,6-dichloro-4-[1,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]phenyl]-2-fluoro-benzamide;M.29.11.k)N-[5-[[2-chloro-6-cyano-4-[1,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide;M.29.11.l)N-[5-[[2-bromo-6-chloro-4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide;M.29.11.m)N-[5-[[2-bromo-6-chloro-4-[1,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide;M.29.11.n)4-cyano-N-[2-cyano-5-[[2,6-dichloro-4-[1,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]phenyl]carbamoyl]phenyl]-2-methyl-benzamide;M.29.11.o)4-cyano-N-[2-cyano-5-[[2,6-dichloro-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]carbamoyl]phenyl]-2-methyl-benzamide;M.29.11.p)N-[5-[[2-bromo-6-chloro-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide;or

a compound selected from the group of M.29.12, wherein the compound isselected from M.29.12a) to M.29.12m): M.29.12.a)2-(1,3-Dioxan-2-yl)-6-[2-(3-pyridinyl)-5-thiazolyl]-pyridine; M.29.12.b)2-[6-[2-(5-Fluoro-3-pyridinyl)-5-thiazolyl]-2-pyridinyl]-pyrimidine;M.29.12.c) 2-[6-[2-(3-Pyridinyl)-5-thiazolyl]-2-pyridinyl]-pyrimidine;M.29.12.d)N-Methylsulfonyl-6-[2-(3-pyridyl)thiazol-5-yl]pyridine-2-carboxamide;M.29.12.e)N-Methylsulfonyl-6-[2-(3-pyridyl)thiazol-5-yl]pyridine-2-carboxamide;M.29.12.f)N-Ethyl-N-[4-methyl-2-(3-pyridyl)thiazol-5-yl]-3-methylthio-propanamide;M.29.12.g)N-Methyl-N-[4-methyl-2-(3-pyridyl)thiazol-5-yl]-3-methylthio-propanamide;M.29.12.h)N,2-Dimethyl-N-[4-methyl-2-(3-pyridyl)thiazol-5-yl]-3-methylthio-propanamide;M.29.12.i)N-Ethyl-2-methyl-N-[4-methyl-2-(3-pyridyl)thiazol-5-yl]-3-methylthio-propanamide;M.29.12j)N-[4-Chloro-2-(3-pyridyl)thiazol-5-yl]-N-ethyl-2-methyl-3-methylthio-propanamide;M.29.12.k)N-[4-Chloro-2-(3-pyridyl)thiazol-5-yl]-N,2-dimethyl-3-methylthio-propanamide;M.29.12.l)N-[4-Chloro-2-(3-pyridyl)thiazol-5-yl]-N-methyl-3-methylthio-propanamide;M.29.12.m)N-[4-Chloro-2-(3-pyridyl)thiazol-5-yl]-N-ethyl-3-methylthio-propanamide;or the compounds

M.29.14a)1-[(6-Chloro-3-pyridinyl)methyl]-1,2,3,5,6,7-hexahydro-5-methoxy-7-methyl-8-nitroimidazo[1,2-a]pyridine;or M.29.14b)1-[(6-Chloropyridin-3-yl)methyl]-7-methyl-8-nitro-1,2,3,5,6,7-hexahydroimidazo[1,2-a]pyridin-5-ol;or the compounds

M.29.16a)1-isopropyl-N,5-dimethyl-N-pyridazin-4-yl-pyrazole-4-carboxamide; orM.29.16b)1-(1,2-dimethylpropyl)-N-ethyl-5-methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide;M.29.16c)N,5-dimethyl-N-pyridazin-4-yl-1-(2,2,2-trifluoro-1-methyl-ethyl)pyrazole-4-carboxamide;M.29.16d)1-[1-(1-cyanocyclopropyl)ethyl]-N-ethyl-5-methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide;M.29.16e)N-ethyl-1-(2-fluoro-1-methyl-propyl)-5-methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide;M.29.16f)1-(1,2-dimethylpropyl)-N,5-dimethyl-N-pyridazin-4-yl-pyrazole-4-carboxamide;M.29.16g)1-[1-(1-cyanocyclopropyl)ethyl]-N,5-dimethyl-N-pyridazin-4-yl-pyrazole-4-carboxamide;M.29.16h)N-methyl-1-(2-fluoro-1-methyl-propyl]-5-methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide;M.29.16i)1-(4,4-difluorocyclohexyl)-N-ethyl-5-methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide;or M.29.16j)1-(4,4-difluorocyclohexyl)-N,5-dimethyl-N-pyridazin-4-yl-pyrazole-4-carboxamide,or

M.29.17 a compound selected from the compounds M.29.17a) to M.29.17j):M.29.17a) N-(1-methylethyl)-2-(3-pyridinyl)-2H-indazole-4-carboxamide;M.29.17b) N-cyclopropyl-2-(3-pyridinyl)-2H-indazole-4-carboxamide;M.29.17c) N-cyclohexyl-2-(3-pyridinyl)-2H-indazole-4-carboxamide;M.29.17d)2-(3-pyridinyl)-N-(2,2,2-trifluoroethyl)-2H-indazole-4-carboxamide;M.29.17e)2-(3-pyridinyl)-N-[(tetrahydro-2-furanyl)methyl]-2H-indazole-5-carboxamide;M.29.17f) methyl2-[[2-(3-pyridinyl)-2H-indazol-5-yl]carbonyl]hydrazinecarboxylate;M.29.17g)N-[(2,2-difluorocyclopropyl)methyl]-2-(3-pyridinyl)-2H-indazole-5-carboxamide;M.29.17h)N-(2,2-difluoropropyl)-2-(3-pyridinyl)-2H-indazole-5-carboxamide;M.29.17i)2-(3-pyridinyl)-N-(2-pyrimidinylmethyl)-2H-indazole-5-carboxamide;M.29.17j)N-[(5-methyl-2-pyrazinyl)methyl]-2-(3-pyridinyl)-2H-indazole-5-carboxamide,or

M.29.18 a compound selected from the compounds M.29.18a) to M.29.18d):M.29.18a)N-[3-chloro-1-(3-pyridyl)pyrazol-4-yl]-N-ethyl-3-(3,3,3-trifluoropropylsulfanyl)propanamide;M.29.18b)N-[3-chloro-1-(3-pyridyl)pyrazol-4-yl]-N-ethyl-3-(3,3,3-trifluoropropylsulfinyl)propanamide;M.29.18c)N-[3-chloro-1-(3-pyridyl)pyrazol-4-yl]-3-[(2,2-difluorocyclopropyl)methylsulfanyl]-N-ethyl-propanamide;M.29.18d)N-[3-chloro-1-(3-pyridyl)pyrazol-4-yl]-3-[(2,2-difluorocyclopropyl)methylsulfinyl]-N-ethyl-propanamide;or the compound

M.29.19 sarolaner, or the compound

M.29.20 lotilaner.

The commercially available compounds of the group M listed above may befound in The Pesticide Manual, 16th Edition, C. MacBean, British CropProtection Council (2013) among other publications. The online PesticideManual is updated regularly and is accessible throughhttp://bcpcdata.com/pesticide-manual.html.

Another online data base for pesticides providing the ISO common namesis http://www.alanwood.net/pesticides.

The M.4 neonicotinoid cycloxaprid is known from WO2010/069266 andWO2011/069456, the neonicotinoid M.4A.2, sometimes also to be named asguadipyr, is known from WO2013/003977, and the neonicotinoid M.4A.3(approved as paichongding in China) is known from WO2007/101369. Themetaflumizone analogue M.228.1 is described in CN10171577 and theanalogue M.228.2 in CN102126994. The phthalamides M.28.1 and M.28.2 areboth known from WO2007/101540. The anthranilamide M.28.3 is described inWO2005/077934. The hydrazide compound M.28.4 is described inWO2007/043677. The anthranilamides M.28.5a) to M.28.5d) and M.28.5h) aredescribed in WO 2007/006670, WO2013/024009 and WO2013/024010, theanthranilamide M.28.5i) is described in WO2011/085575, M.28.5j) inWO2008/134969, M.28.5k) in US2011/046186 and M.28.51) in WO2012/034403.The diamide compound M.28.6 can be found in WO2012/034472. Thespiroketal-substituted cyclic ketoenol derivative M.29.3 is known fromWO2006/089633 and the biphenyl-substituted spirocyclic ketoenolderivative M.29.4 from WO2008/067911. The triazoylphenylsulfide M.29.5is described in WO2006/043635, and biological control agents on thebasis of Bacillus firmus are described in WO2009/124707. The compoundsM.29.6a) to M.29.6i) listed under M.29.6 are described in WO2012/029672,and M.29.6j) and M.29.6k) in WO2013/129688. The nematicide M.29.8 isknown from WO2013/055584. The isoxazoline M.29.9.a) is described inWO2013/050317. The isoxazoline M.29.9.b) is described in WO2014/126208.The pyridalyl-type analogue M.29.10 is known from WO2010/060379. Thecarboxamides broflanilide and M.29.11.b) to M.29.11.h) are described inWO2010/018714, and the carboxamides M.29.11i) to M.29.11.p) inWO2010/127926. The pyridylthiazoles M.29.12.a) to M.29.12.c) are knownfrom WO2010/006713, M.29.12.d) and M.29.12.e) are known fromWO2012/000896, and M.29.12.f) to M.29.12.m) from WO2010/129497. Thecompounds M.29.14a) and M.29.14b) are known from WO2007/101369. Thepyrazoles M.29.16.a) to M.29.16h) are described in WO2010/034737,WO2012/084670, and WO2012/143317, respectively, and the pyrazolesM.29.16i) and M.29.16j) are described in U.S. 61/891,437. Thepyridinylindazoles M.29.17a) to M.29.17.j) are described inWO2015/038503. The pyridylpyrazoles M.29.18a) to M.29.18d) are describedin US2014/0213448. The isoxazoline M.29.19 is described inWO2014/036056. The isoxazoline M.29.20 is known from WO2014/090918.

The following list of fungicides, in conjunction with which thecompounds of the present invention can be used, is intended toillustrate the possible combinations but does not limit them:

A) Respiration Inhibitors

-   -   Inhibitors of complex III at Q_(o) site (e. g. strobilurins):        azoxystrobin (A.1.1), coumethoxystrobin (A.1.2), coumoxystrobin        (A.1.3), dimoxystrobin (A.1.4), enestroburin (A.1.5),        fenaminstrobin (A.1.6), fenoxystrobin/flufenoxystrobin (A.1.7),        fluoxastrobin (A.1.8), kresoxim-methyl (A.1.9), mandestrobin        (A.1.10), metominostrobin (A.1.11), orysastrobin (A.1.12),        picoxy.strobin (A.1.13), pyraclostrobin (A.1.14),        pyrametostrobin (A.1.15), pyraoxystrobin (A.1.16),        trifloxystrobin (A.1.17),        2-(2-(3-(2,6-dichlorophenyl)-1-methyl-allylideneaminooxymethyl)-phenyl)-2-methoxyimino-N-methyl-acetamide        (A.1.18), pyribencarb (A.1.19), triclopyricarb/chlorodincarb        (A.1.20), famoxadone (A.1.21), fenamidone (A.1.21),        methyl-N-[2-[(1,4-dimethyl-5-phenyl-pyrazol-3-yl)oxylmethyl]phenyl]-N-methoxy-carbamate        (A.1.22),        1-[3-chloro-2-[[1-(4-chlorophenyl)-1H-pyrazol-3-yl]oxymethyl]phenyl]-4-methyl-tetrazol-5-one        (A.1.23),        1-[3-bromo-2-[[1-(4-chlorophenyl)pyrazol-3-yl]oxymethyl]phenyl]-4-methyl-tetrazol-5-one        (A.1.24),        1-[2-[[1-(4-chlorophenyl)pyrazol-3-yl]oxymethyl]-3-methyl-phenyl]-4-methyl-tetrazol-5-one        (A.1.25),        1-[2-[[1-(4-chlorophenyl)pyrazol-3-yl]oxymethyl]-3-fluoro-phenyl]-4-methyl-tetrazol-5-one        (A.1.26),        1-[2-[[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxymethyl]-3-fluoro-phenyl]-4-methyl-tetrazol-5-one        (A.1.27),        1-[2-[[4-(4-chlorophenyl)thiazol-2-yl]oxymethyl]-3-methyl-phenyl]-4-methyl-tetrazol-5-one        (A.1.28),        1-[3-chloro-2-[[4-(p-tolyl)thiazol-2-yl]oxymethyl]phenyl]-4-methyl-tetrazol-5-one        (A.1.29),        1-[3-cyclopropyl-2-[[2-methyl-4-(1-methylpyrazol-3-yl)phenoxy]methyl]phenyl]-4-methyl-tetrazol-5-one        (A.1.30),        1-[3-(difluoromethoxy)-2-[[2-methyl-4-(1-methylpyrazol-3-yl)phenoxy]methyl]phenyl]-4-methyl-tetrazol-5-one        (A.1.31),        1-methyl-4-[3-methyl-2-[[2-methyl-4-(1-methylpyrazol-3-yl)phenoxy]methyl]phenyl]tetrazol-5-one        (A.1.32),        1-methyl-4-[3-methyl-2-[[1-[3-(trifluoromethyl)phenyl]-ethylideneamino]oxymethyl]phenyl]tetrazol-5-one        (A.1.33),        (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]-oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide        (A.1.34),        (Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide        (A.1.35),        (Z,2E)-5-[1-(4-chloro-2-fluoro-phenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide        (A.1.36),    -   inhibitors of complex Ill at Q_(i) site: cyazofamid (A.2.1),        amisulbrom (A.2.2),        [(3S,6S,7R,8R)-8-benzyl-3-[(3-acetoxy-4-methoxy-pyridine-2-carbonyl)amino]-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl]        2-methylpropanoate (A.2.3),        [(3S,6S,7R,8R)-8-benzyl-3-[[3-(acetoxymethoxy)-4-methoxypyridine-2-carbonyl]amino]-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl]        2-methylpropanoate (A.2.4),        [(3S,6S,7R,8R)-8-benzyl-3-[(3-isobutoxycarbonyloxy-4-methoxy-pyridine-2-carbonyl)amino]-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl]        2-methylpropanoate (A.2.5),        [(3S,6S,7R,8R)-8-benzyl-3-[[3-(1,3-benzodioxol-5-ylmethoxy)-4-methoxy-pyridine-2-carbonyl]amino]-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl]        2-methylpropanoate (A.2.6);        (3S,6S,7R,8R)-3-[[(3-hydroxy-4-methoxy-2-pyridinyl)carbonyl]amino]-6-methyl-4,9-dioxo-8-(phenylmethyl)-1,5-dioxonan-7-yl        2-methylpropanoate (A.2.7),        (3S,6S,7R,8R)-8-benzyl-3-[3-[(isobutyryloxy)methoxy]-4-methoxypicolinamido]-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl        isobutyrate (A.2.8);    -   inhibitors of complex II (e. g. carboxamides): benodanil        (A.3.1), benzovindiflupyr (A.3.2), bixafen (A.3.3), boscalid        (A.3.4), carboxin (A.3.5), fenfuram (A.3.6), fluopyram (A.3.7),        flutolanil (A.3.8), fluxapyroxad (A.3.9), furametpyr (A.3.10),        isofetamid (A.3.11), isopyrazam (A.3.12), mepronil (A.3.13),        oxycarboxin (A.3.14), penflufen (A.3.14), penthiopyrad (A.3.15),        sedaxane (A.3.16), tecloftalam (A.3.17), thifluzamide (A.3.18),        N-(4′-trifluoromethylthiobiphenyl-2-yl)-3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide        (A.3.19),        N-(2-(1,3,3-trimethyl-butyl)-phenyl)-1,3-dimethyl-5-fluoro-1H-pyrazole-4-carboxamide        (A.3.20),        3-(difluoromethyl)-1-methyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide        (A.3.21),        3-(trifluoromethyl)-1-methyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide        (A.3.22),        1,3-dimethyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide        (A.3.23),        3-(trifluoromethyl)-1,5-dimethyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide        (A.3.24),        1,3,5-trimethyl-N-(1,1,3-trimethylindan-4-yl)pyrazole-4-carboxamide        (A.3.25),        N-(7-fluoro-1,1,3-trimethyl-indan-4-yl)-1,3-dimethyl-pyrazole-4-carboxamide        (A.3.26),        N-[2-(2,4-dichlorophenyl)-2-methoxy-1-methyl-ethyl]-3-(difluoromethyl)-1-methyl-pyrazole-4-carboxamide        (A.3.27);    -   other respiration inhibitors (e. g. complex I, uncouplers):        diflumetorim (A.4.1),        (5,8-difluoroquinazolin-4-yl)-{2-[2-fluoro-4-(4-trifluoromethylpyridin-2-yloxy)-phenyl]-ethyl}-amine        (A.4.2); nitrophenyl derivates: binapacryl (A.4.3), dinobuton        (A.4.4), dinocap (A.4.5), fluazinam (A.4.6); ferimzone (A.4.7);        organometal compounds: fentin salts, such as fentin-acetate        (A.4.8), fentin chloride (A.4.9) or fentin hydroxide (A.4.10);        ametoctradin (A.4.11); and silthiofam (A.4.12);

B) Sterol Biosynthesis Inhibitors (SBI Fungicides)

-   -   C14 demethylase inhibitors (DMI fungicides): triazoles:        azaconazole (B.1.1), bitertanol (B.1.2), bromuconazole (B.1.3),        cyproconazole (B.1.4), difenoconazole (B.1.5), diniconazole        (B.1.6), diniconazole-M (B.1.7), epoxiconazole (B.1.8),        fenbuconazole (B.1.9), fluquinconazole (B.1.10), flusilazole        (B.1.11), flutriafol (B.1.12), hexaconazole (B.1.13),        imibenconazole (B.1.14), ipconazole (B.1.15), metconazole        (B.1.17), myclobutanil (B.1.18), oxpoconazole (B.1.19),        paclobutrazole (B.1.20), penconazole (B.1.21), propiconazole        (B.1.22), prothioconazole (B.1.23), simeconazole (B.1.24),        tebuconazole (B.1.25), tetraconazole (B.1.26), triadimefon        (B.1.27), triadimenol (B.1.28), triticonazole (B.1.29),        uniconazole (B.1.30),        1-[rel-(2S,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)-oxiranylmethyl]-5-thiocyanato-1H-[1,2,4]triazolo        (B.1.31),        2-[rel-(2S,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)-oxiranylmethyl]-2H-[1,2,4]triazole-3-thiol        (B.1.32),        2-[2-chloro-4-(4-chlorophenoxy)phenyl]-1-(1,2,4-triazol-1-yl)pentan-2-ol        (B.1.33),        1-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-cyclopropyl-2-(1,2,4-triazol-1-yl)ethanol        (B.1.34),        2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1,2,4-triazol-1-yl)butan-2-ol        (B.1.35),        2-[2-chloro-4-(4-chlorophenoxy)phenyl]-1-(1,2,4-triazol-1-yl)butan-2-ol        (B.1.36),        2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-3-methyl-1-(1,2,4-triazol-1-yl)butan-2-ol        (B.1.37),        2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1,2,4-triazol-1-yl)propan-2-ol        (B.1.38),        2-[2-chloro-4-(4-chlorophenoxy)phenyl]-3-methyl-1-(1,2,4-triazol-1-yl)butan-2-ol        (B.1.39),        2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1,2,4-triazol-1-yl)pentan-2-ol        (B.1.40),        2-[4-(4-fluorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1,2,4-triazol-1-yl)propan-2-ol        (B.1.41),        2-[2-chloro-4-(4-chlorophenoxy)phenyl]-1-(1,2,4-triazol-1-yl)pent-3-yn-2-ol        (B.1.51); imidazoles: imazalil (B.1.42), pefurazoate (B.1.43),        prochloraz (B.1.44), triflumizol (B.1.45); pyrimidines,        pyridines and piperazines: fenarimol (B.1.46), nuarimol        (B.1.47), pyrifenox (B.1.48), triforine (B.1.49),        [3-(4-chloro-2-fluoro-phenyl)-5-(2,4-difluorophenyl)isoxazol-4-yl]-(3-pyridyl)methanol        (B.1.50);    -   Delta14-reductase inhibitors: aldimorph (B.2.1), dodemorph        (B.2.2), dodemorph-acetate (B.2.3), fenpropimorph (B.2.4),        tridemorph (B.2.5), fenpropidin (B.2.6), piperalin (B.2.7),        spiroxamine (B.2.8);    -   Inhibitors of 3-keto reductase: fenhexamid (B.3.1);

C) Nucleic Acid Synthesis Inhibitors

-   -   phenylamides or acyl amino acid fungicides: benalaxyl (C.1.1),        benalaxyl-M (C.1.2), kiralaxyl (C.1.3), metalaxyl (C.1.4),        metalaxyl-M (mefenoxam, C.1.5), ofurace (C.1.6), oxadixyl        (C.1.7);    -   others: hymexazole (C.2.1), octhilinone (C.2.2), oxolinic acid        (C.2.3), bupirimate (C.2.4), 5-fluorocytosine (C.2.5),        5-fluoro-2-(p-tolylmethoxy)pyrimidin-4-amine (C.2.6),        5-fluoro-2-(4-fluorophenylmethoxy)pyrimidin-4-amine (C.2.7);

D) Inhibitors of Cell Division and Cytoskeleton

-   -   tubulin inhibitors, such as benzimidazoles, thiophanates:        benomyl (D1.1), carbendazim (D1.2), fuberidazole (D1.3),        thiabendazole (D1.4), thiophanate-methyl (D1.5);        triazolopyrimidines:        5-chloro-7-(4-methylpiperidin-1-yl)-6-(2,4,6-trifluorophenyl)[1,2,4]triazolo[1,5-a]pyrimidine        (D1.6);    -   other cell division inhibitors: diethofencarb (D2.1), ethaboxam        (D2.2), pencycuron (D2.3), fluopicolide (D2.4), zoxamide (D2.5),        metrafenone (D2.6), pyriofenone (D2.7);

E) Inhibitors of Amino Acid and Protein Synthesis

-   -   methionine synthesis inhibitors (anilino-pyrimidines):        cyprodinil (E.1.1), mepanipyrim (E.1.2), pyrimethanil (E.1.3);    -   protein synthesis inhibitors: blasticidin-S(E.2.1), kasugamycin        (E.2.2), kasugamycin hydrochloride-hydrate (E.2.3), mildiomycin        (E.2.4), streptomycin (E.2.5), oxytetracyclin (E.2.6), polyoxine        (E.2.7), validamycin A (E.2.8);

F) Signal Transduction Inhibitors

-   -   MAP/histidine kinase inhibitors: fluoroimid (F.1.1), iprodione        (F.1.2), procymidone (F.1.3), vinclozolin (F.1.4), fenpiclonil        (F.1.5), fludioxonil (F.1.6);    -   G protein inhibitors: quinoxyfen (F.2.1);

G) Lipid and Membrane Synthesis Inhibitors

-   -   Phospholipid biosynthesis inhibitors: edifenphos (G.1.1),        iprobenfos (G.1.2), pyrazophos (G.1.3), isoprothiolane (G.1.4);    -   lipid peroxidation: dicloran (G.2.1), quintozene (G.2.2),        tecnazene (G.2.3), tolclofos-methyl (G.2.4), biphenyl (G.2.5),        chloroneb (G.2.6), etridiazole (G.2.7);    -   phospholipid biosynthesis and cell wall deposition: dimethomorph        (G.3.1), flumorph (G.3.2), mandipropamid (G.3.3), pyrimorph        (G.3.4), benthiavalicarb (G.3.5), iprovalicarb (G.3.6),        valifenalate (G.3.7) and        N-(1-(1-(4-cyano-phenypethanesulfonyl)-but-2-yl) carbamic        acid-(4-fluorophenyl) ester (G.3.8);    -   compounds affecting cell membrane permeability and fatty acids:        propamocarb (G.4.1);    -   fatty acid amide hydrolase inhibitors: oxathiapiprolin (G.5.1),        2-{3-[2-(1-{[3,5-bis(difluoromethyl-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}phenyl        methanesulfonate (G.5.2),        2-{3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)        1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}-3-chlorophenyl        methanesulfonate (G.5.3);

H) Inhibitors with Multi Site Action

-   -   inorganic active substances: Bordeaux mixture (H.1.1), copper        acetate (H.1.2), copper hydroxide (H.1.3), copper oxychloride        (H.1.4), basic copper sulfate (H.1.5), sulfur (H.1.6);    -   thio- and dithiocarbamates: ferbam (H.2.1), mancozeb (H.2.2),        maneb (H.2.3), metam (H.2.4), metiram (H.2.5), propineb (H.2.6),        thiram (H.2.7), zineb (H.2.8), ziram (H.2.9);    -   organochlorine compounds (e. g. phthalimides, sulfamides,        chloronitriles): anilazine (H.3.1), chlorothalonil (H.3.2),        captafol (H.3.3), captan (H.3.4), folpet (H.3.5), dichlofluanid        (H.3.6), dichlorophen (H.3.7), hexachlorobenzene (H.3.8),        pentachlorphenole (H.3.9) and its salts, phthalide (H.3.10),        tolylfluanid (H.3.11),        N-(4-chloro-2-nitro-phenyl)-N-ethyl-4-methylbenzenesulfonamide        (H.3.12);    -   guanidines and others: guanidine (H.4.1), dodine (H.4.2), dodine        free base (H.4.3), guazatine (H.4.4), guazatine-acetate (H.4.5),        iminoctadine (H.4.6), iminoctadine-triacetate (H.4.7),        iminoctadine-tris(albesilate) (H.4.8), dithianon (H.4.9),        2,6-dimethyl-1H,5H-[1,4]dithiino[2,3-c:5,6-c′]dipyrrole-1,3,5,7(2H,6H)-tetraone        (H.4.10);

I) Cell Wall Synthesis Inhibitors

-   -   inhibitors of glucan synthesis: validamycin (1.1.1), polyoxin B        (1.1.2);    -   melanin synthesis inhibitors: pyroquilon (1.2.1), tricyclazole        (1.2.2), carpropamid (1.2.3), dicyclomet (1.2.4), fenoxanil        (1.2.5);

J) Plant Defence Inducers

-   -   acibenzolar-S-methyl (J.1.1), probenazole (J.1.2), isotianil        (J.1.3), tiadinil (J.1.4), prohexadione-calcium (J.1.5);        phosphonates: fosetyl (J.1.6), fosetyl-aluminum (J.1.7),        phosphorous acid and its salts (J.1.8), potassium or sodium        bicarbonate (J.1.9);

K) Unknown Mode of Action

-   -   bronopol (K.1.1), chinomethionat (K.1.2), cyflufenamid (K.1.3),        cymoxanil (K.1.4), dazomet (K.1.5), debacarb (K.1.6),        diclomezine (K.1.7), difenzoquat (K.1.8),        difenzoquat-methylsulfate (K.1.9), diphenylamin (K.1.10),        fenpyrazamine (K.1.11), flumetover (K.1.12), flusulfamide        (K.1.13), flutianil (K.1.14), methasulfocarb (K.1.15),        nitrapyrin (K.1.16), nitrothal-isopropyl (K.1.18),        oxathiapiprolin (K.1.19), tolprocarb (K.1.20), oxin-copper        (K.1.21), proquinazid (K.1.22), tebufloquin (K.1.23),        tecloftalam (K.1.24), triazoxide (K.1.25),        2-butoxy-6-iodo-3-propylchromen-4-one (K.1.26),        2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{5-[2-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone        (K.1.27),        2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{5-[2-fluoro-6-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone        (K.1.28),        2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{5-[2-chloro-6-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone        (K.1.29),        N-(cyclopropylmethoxyimino-(6-difluoro-methoxy-2,3-difluoro-phenyl)-methyl)-2-phenyl        acetamide (K.1.30),        N′-(4-(4-chloro-3-trifluoromethyl-phenoxy)-2,5-dimethyl-phenyl)-N-ethyl-N-methyl        formamidine (K.1.31),        N′-(4-(4-fluoro-3-trifluoromethyl-phenoxy)-2,5-dimethyl-phenyl)-N-ethyl-N-methyl        formamidine (K.1.32),        N′-(2-methyl-5-trifluoromethyl-4-(3-trimethylsilanyl-propoxy)-phenyl)-N-ethyl-N-methyl        formamidine (K.1.33),        N′-(5-difluoromethyl-2-methyl-4-(3-trimethylsilanyl-propoxy)-phenyl)-N-ethyl-N-methyl        formamidine (K.1.34), methoxy-acetic acid        6-tert-butyl-8-fluoro-2,3-dimethyl-quinolin-4-yl ester (K.1.35),        3-[5-(4-methylphenyl)-2,3-dimethyl-isoxazolidin-3-yl]-pyridine        (K.1.36),        3-[5-(4-chloro-phenyl)-2,3-dimethyl-isoxazolidin-3-yl]-pyridine        (pyrisoxazole) (K.1.37), N-(6-methoxy-pyridin-3-yl)        cyclopropane-carboxylic acid amide (K.1.38),        5-chloro-1-(4,6-dimethoxy-pyrimidin-2-yl)-2-methyl-1H-benzoimidazole        (K.1.39),        2-(4-chloro-phenyl)-N-[4-(3,4-dimethoxy-phenyl)-isoxazol-5-yl]-2-prop-2-ynyloxy-acetamide,        ethyl (Z)-3-amino-2-cyano-3-phenyl-prop-2-enoate (K.1.40),        picarbutrazox (K.1.41), pentyl        N-[6-[[(Z)-[(1-methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]carbamate        (K.1.42),        2-[2-[(7,8-difluoro-2-methyl-3-quinolyl)oxy]-6-fluoro-phenyl]propan-2-01        (K.1.43),        2-[2-fluoro-6-[(8-fluoro-2-methyl-3-quinolyl)oxy]phen-yl]propan-2-ol        (K.1.44),        3-(5-fluoro-3,3,4,4-tetramethyl-3,4-dihydroisoquinolin-1-yl)quinoline        (K.1.45),        3-(4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinoline        (K.1.46),        3-(4,4,5-trifluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinoline        (K.1.47),        9-fluoro-2,2-dimethyl-5-(3-quinolyl)-3H-1,4-benzoxazepine        (K.1.48).

The fungicides described by common names, their preparation and theiractivity e.g. against harmful fungi is known (cf.:http://www.alanwood.net/pesticides/); these substances are commerciallyavailable.

The fungicides described by IUPAC nomenclature, their preparation andtheir pesticidal activity is also known (cf. Can. J. Plant Sci. 48(6),587-94, 1968; EP-A 141 317; EP-A 152 031; EP-A 226 917; EP-A 243 970;EP-A 256 503; EP-A 428 941; EP-A 532 022; EP-A 1 028 125; EP-A 1 035122; EP-A 1 201 648; EP-A 1 122 244, JP 2002316902; DE 19650197; DE10021412; DE 102005009458; U.S. Pat. Nos. 3,296,272; 3,325,503; WO98/46608; WO 99/14187; WO 99/24413; WO 99/27783; WO 00/29404; WO00/46148; WO 00/65913; WO 01/54501; WO 01/56358; WO 02/22583; WO02/40431; WO 03/10149; WO 03/11853; WO 03/14103; WO 03/16286; WO03/53145; WO 03/61388; WO 03/66609; WO 03/74491; WO 04/49804; WO04/83193; WO 05/120234; WO 05/123689; WO 05/123690; WO 05/63721; WO05/87772; WO 05/87773; WO 06/15866; WO 06/87325; WO 06/87343; WO07/82098; WO 07/90624, WO 11/028657, WO2012/168188, WO 2007/006670, WO2011/77514; WO13/047749, WO 10/069882, WO 13/047441, WO 03/16303, WO09/90181, WO 13/007767, WO 13/010862, WO 13/127704, WO 13/024009, WO13/024010 and WO 13/047441, WO 13/162072, WO 13/092224, WO 11/135833).

Biopesticides

Suitable mixing partners for the compounds of the present invention alsoinclude biopesticides.

Biopesticides have been defined as a form of pesticides based onmicro-organisms (bacteria, fungi, viruses, nematodes, etc.) or naturalproducts (compounds, such as metabolites, proteins, or extracts frombiological or other natural sources) (U.S. Environmental ProtectionAgency: http://www.epa.gov/pesticides/biopesticides/). Biopesticidesfall into two major classes, microbial and biochemical pesticides:

(1) Microbial pesticides consist of bacteria, fungi or viruses (andoften include the metabolites that bacteria and fungi produce).Entomopathogenic nematodes are also classified as microbial pesticides,even though they are multi-cellular.

(2) Biochemical pesticides are naturally occurring substances orstructurally-similar and functionally identical to a naturally-occurringsubstance and extracts from biological sources that control pests orprovide other crop protection uses as defined below, but have non-toxicmode of actions (such as growth or developmental regulation,attractents, repellents or defense activators (e.g. induced resistance)and are relatively non-toxic to mammals.

Biopesticides for use against crop diseases have already establishedthemselves on a variety of crops. For example, biopesticides alreadyplay an important role in controlling downy mildew diseases. Theirbenefits include: a 0-Day Pre-Harvest Interval, the ability to use undermoderate to severe disease pressure, and the ability to use in mixtureor in a rotational program with other registered pesticides.

A major growth area for biopesticides is in the area of seed treatmentsand soil amendments. Biopesticidal seed treatments are e.g. used tocontrol soil borne fungal pathogens that cause seed rots, damping-off,root rot and seedling blights. They can also be used to control internalseed borne fungal pathogens as well as fungal pathogens that are on thesurface of the seed. Many biopesticidal products also show capacities tostimulate plant host defenses and other physiological processes that canmake treated crops more resistant to a variety of biotic and abioticstresses or can regulate plant growth. Many biopesticidal products alsoshow capacities to stimulate plant health, plant growth and/or yieldenhancing activity.

The following list of biopesticides, in conjunction with which thecompounds of the present invention can be used, is intended toillustrate the possible combinations but does not limit them:

L) Biopesticides

L1) Microbial pesticides with fungicidal, bactericidal, viricidal and/orplant defense activator activity: Ampelomyces quisqualis, Aspergillusflavus, Aureobasidium pullulans, Bacillus altitudinis; B.amyloliquefaciens, B. megaterium, B. mojavensls; B. mycoldes, B.pumilus, B. simplex, B. solisalsi, B. subtilis, B. subtilis var.amyloliquefaciens, Candida oleophila, C. saitoana, Clavibactermichiganensis (bacteriophages), Coniothyrium minitans, Cryphonectriaparasitica, Cryptococcus albidus, Dilophosphora alopecuri, Fusariumoxysporum, Clonostachys rosea f. catenulate (also named Gilocladlumcatenulatum), Gliocladium roseum, Lysobacter antibioticus, L.enzymogenes, Metschnikowla fructicola, Microdochlum climerum,Microsphaeropsis ochracea, Muscodor albus, Paenibacillus alvei,Paenibacillus polymyxa, Pantoea vagans, Penicillium bilaiae, Phleblopsisgigantea, Pseudomonas sp., Pseudomonas chloraphls, Pseudozymaflocculosa, Pichia aromala, Pythium ollgandrum, Sphaerodesmycoparasitica, Streptomyces griseoviridis; S. lydicus, S.violaceusniger, Talaromyces flavus, Trichoderma asperelloides, T.asperellum, T. atroviride, T. fertile, T. gamsli, T. harmatum, T.harzianum, T. polysporum, T. stromaticum, T. virens, T. wide, Typhulaphacorrhiza, Ulocladium ouclemansii Verticillium dahlia, zucchini yellowmosaic virus (avirulent strain);

L2) Biochemical pesticides with fungicidal, bactericidal, viricidaland/or plant defense activator activity: harpin protein, Reynoutriasachalinensis extract;

L3) Microbial pesticides with insecticidal, acaricidal, molluscidaland/or nematicidal activity: Agrobacterium radiobacter, Bacillus cereus,B. firmus, B. thuringiensis, B. thuringiensis ssp. aizawai B. t. ssp.israelensis, B. t. ssp. galleriae, B. t. ssp. kurstakt; B. t. ssp.tenebrionis, Beauveria bassiana, B. brongniartii, Burkholderia spp.,Chromobacterium subtsugae, Cydia pomonella granulovirus (CpGV),Cryptophlebia leucotreta granulovirus (CrleGV), Flavobacterium spp.,Helicoverpa armigera nucleopolyhedrovirus (HearNPV), Helicoverpa zeanucleopolyhedrovirus (HzNPV), Helicoverpa zea single capsidnucleopolyhedrovirus (HzSNPV), Heterorhabditis bacteriophora, Isariafumosorosea, Lecanicillium longisporum, L. muscarium, Metarhiziumanisopliae, Metarhizium anisopliae var. anisopliae, M. anisopliae var.acridum, Nomuraea rileyi, Paecilomyces fumosoroseus, P. Illacinus,Paenibacillus popilliae, Pasteuria spp., P. nishizawae, P. penetrans, P.ramosa, P. thornea, P. usgae, Pseudomonas fluorescens, Spodopteralittoralis nucleopolyhedrovirus (SpliNPV), Steinernema carpocapsae, S.feltiae, S. kraussei; Streptomyces galbus, S. microfiavus,

L4) Biochemical pesticides with insecticidal, acaricidal, molluscidal,pheromone and/or nematicidal activity: L-carvone, citral,(E,Z)-7,9-dodecadien-1-yl acetate, ethyl formate, (E,Z)-2,4-ethyldecadienoate (pear ester), (Z,Z,E)-7,11,13-hexadecatrienal, heptylbutyrate, isopropyl myristate, lavanulyl senecioate, cis-jasmone,2-methyl 1-butanol, methyl eugenol, methyl jasmonate,(E,Z)-2,13-octadecadien-1-ol, (E,Z)-2,13-octadecadien-1-ol acetate,(E,Z)-3,13-octadecadien-1-ol, R-1-octen-3-ol, pentatermanone,(E,Z,Z)-3,8,11-tetradecatrienyl acetate, (Z,E)-9,12-tetradecadien-1-ylacetate, Z-7-tetradecen-2-one, Z-9-tetradecen-1-yl acetate,Z-11-tetradecenal, Z-11-tetradecen-1-ol, extract of Chenopodiumambrosiodes, Neem oil, Quillay extract;

L5) Microbial pesticides with plant stress reducing, plant growthregulator, plant growth promoting and/or yield enhancing activity:Azospirillum amazonense, A. brasilense, A. lipoferum, A. irakense, A.halopraeferens, Bradyrhizobium spp., B. elkanii, B. Japonicum, B.liaoningense, B. lupine; Delftia acidovorans, Glomus intraradices,Mesorhizobium spp., Rhizobium leguminosarum bv. phaseoli, R. I. bv.trifolii, R. I. bv. viciae, R. tropic, Sinorhizobium mellloti.

The biopesticides from group L1) and/or L2) may also have insecticidal,acaricidal, molluscidal, pheromone, nematicidal, plant stress reducing,plant growth regulator, plant growth promoting and/or yield enhancingactivity. The biopesticides from group L3) and/or L4) may also havefungicidal, bactericidal, viricidal, plant defense activator, plantstress reducing, plant growth regulator, plant growth promoting and/oryield enhancing activity. The biopesticides from group L5) may also havefungicidal, bactericidal, viricidal, plant defense activator,insecticidal, acaricidal, molluscidal, pheromone and/or nematicidalactivity.

Many of these biopesticides have been deposited under deposition numbersmentioned herein (the prefices such as ATCC or DSM refer to the acronymof the respective culture collection, for details see e. g. here:http://www.wfcc.info/ccinfo/collection/by_acronym/), are referred to inliterature, registered and/or are commercially available: mixtures ofAureobasidium pullulans DSM 14940 and DSM 14941 isolated in 1989 inKonstanz, Germany (e. g. blastospores in Blossom-Protect® from bio-fermGmbH, Austria), Azosplrillum brasllense Sp245 originally isolated inwheat reagion of South Brazil (Passo Fundo) at least prior to 1980 (BR11005; e. g. GELFIX® Gramineas from BASF Agricultural Specialties Ltd.,Brazil), A. brasllense strains Ab-V5 and Ab-V6 (e. g. in AzoMax fromNovozymes BioAg Produtos papra Agricultura Ltda., Quattro Barras, Brazilor Simbiose-Maíz® from Simbiose-Agro, Brazil; Plant Soil 331, 413-425,2010), Bacillus amyloliquefaciens strain AP-188 (NRRL B-50615 andB-50331; U.S. Pat. No. 8,445,255); B. amyloliquefaciens spp. plantarumD747 isolated from air in Kikugawa-shi, Japan (US 20130236522 A1; FERMBP-8234; e. g. Double Nickel™ 55 WDG from Certis LLC, USA), B.amyloliquefaciens spp. plantarum FZB24 isolated from soil inBrandenburg, Germany (also called 5133615; DSM 96-2; J. Plant Dis. Prot.105, 181-197, 1998; e. g. Taegro® from Novozyme Biologicals, Inc., USA),B. amyloliquefaciens ssp. plantarum FZB42 isolated from soil inBrandenburg, Germany (DSM 23117; J. Plant Dis. Prot. 105, 181-197, 1998;e. g. RhizoVital® 42 from AbiTEP GmbH, Germany), B. amyloliquefaciensssp. plantarum MBI600 isolated from faba bean in Sutton Bonington,Nottinghamshire, U.K. at least before 1988 (also called 1430; NRRLB-50595; US 2012/0149571 A1; e. g. Integral® from BASF Corp., USA), B.amyloliquefaciens spp. plantarum QST-713 isolated from peach orchard in1995 in California, U.S.A. (NRRL B-21661; e. g. Serenade® MAX from BayerCrop Science LP, USA), B. amyloliquefaciens spp. plantarum TJ1000isolated in 1992 in South Dakoda, U.S.A. (also called 1BE; ATCC BAA-390;CA 2471555 A1; e. g. QuickRoots™ from TJ Technologies, Watertown, S.Dak., USA), B. firmus CNCM 1-1582, a variant of parental strain EIP-N1(CNCM 1-1556) isolated from soil of central plain area of Israel (WO2009/126473, U.S. Pat. No. 6,406,690; e. g. Votivo® from BayerCropScience LP, USA), B. pumilus GHA 180 isolated from apple treerhizosphere in Mexico (IDAC 260707-01; e. g. PRO-MIX® BX from PremierHorticulture, Quebec, Canada), B. pumilus INR-7 otherwise referred to asBU-F22 and BU-F33 isolated at least before 1993 from cucumber infestedby Erwinia tracheiphila (NRRL B-50185, NRRL B-50153; U.S. Pat. No.8,445,255), (NRRL B-50754; WO 2014/029697; B. pumilus QST 2808 wasisolated from soil collected in Pohnpei, Federated States of Micronesia,in 1998 (NRRL B-30087; e. g. Sonata® or Ballad® Plus from Bayer CropScience LP, USA), B. simplex ABU 288 (NRRL B-50304; U.S. Pat. No.8,445,255), B. subtilis FB17 also called UD 1022 or UD10-22 isolatedfrom red beet roots in North America (ATCC PTA-11857; System. Appl.Microbiol. 27, 372-379, 2004; US 2010/0260735; WO 2011/109395); B.thuringiensis ssp. aizawai ABTS-1857 isolated from soil taken from alawn in Ephraim, Wis., U.S.A., in 1987 (also called ABG-6346; ATCCSD-1372; e. g. XenTari® from BioFa AG, Münsingen, Germany), B. t. ssp.kurstaki ABTS-351 identical to HD-1 isolated in 1967 from diseased PinkBollworm black larvae in Brownsville, Tex., U.S.A. (ATCC SD-1275; e. g.Dipel® DF from Valent BioSciences, IL, USA), B. t. ssp. kurstaki SB4isolated from E. saccharina larval cadavers (NRRL B-50753; B. t. ssp.tenebrionis NB-176-1, a mutant of strain NB-125, a wild type strainisolated in 1982 from a dead pupa of the beetle Tenebrio molitor (DSM5480; EP 585 215 B1; e. g. Novodor® from Valent BioSciences,Switzerland), Beauveria bassiana GHA (ATCC 74250; e. g. BotaniGard®22WGP from Laverlam Int. Corp., USA), B. bassiana JW-1 (ATCC 74040; e.g. Naturalis® from CBC (Europe) S.r.l., Italy), B. bassiana PPRI 5339isolated from the larva of the tortoise beetle Conchyloctenia punctata(NRRL 50757), Bradyrhizobium elkanii strains SEMIA 5019 (also called29W) isolated in Rio de Janeiro, Brazil and SEMIA 587 isolated in 1967in the State of Rio Grande do Sul, from an area previously inoculatedwith a North American isolate, and used in commercial inoculants since1968 (Appl. Environ. Microbiol. 73(8), 2635, 2007; e. g. GELFIX 5 fromBASF Agricultural Specialties Ltd., Brazil), B. japonicum 532c isolatedfrom Wisconsin field in U.S.A. (Nitragin 61A152; Can. J. Plant. Sci. 70,661-666, 1990; e. g. in Rhizoflo®, Histick®, Hicoat® Super from BASFAgricultural Specialties Ltd., Canada), B. japonicum E-109 variant ofstrain USDA 138 (INTA E109, SEMIA 5085; Eur. J. Soil Biol. 45, 28-35,2009; Biol. Fertil. Soils 47, 81-89, 2011); B. japonicum strainsdeposited at SEMIA known from Appl. Environ. Microbiol. 73(8), 2635,2007: SEMIA 5079 isolated from soil in Cerrados region, Brazil byEmbrapa-Cerrados used in commercial inoculants since 1992 (CPAC 15; e.g. GELFIX 5 or ADHERE 60 from BASF Agricultural Specialties Ltd.,Brazil), B. japonicum SEMIA 5080 obtained under lab conditions byEmbrapa-Cerrados in Brazil and used in commercial inoculants since 1992,being a natural variant of SEMIA 586 (CB1809) originally isolated inU.S.A. (CPAC 7; e. g. GELFIX 5 or ADHERE 60 from BASF AgriculturalSpecialties Ltd., Brazil); Burkholderia sp. A396 isolated from soil inNikko, Japan, in 2008 (NRRL B-50319; WO 2013/032693; Marrone BioInnovations, Inc., USA), Coniothyrium minitans CON/M/91-08 isolated fromoilseed rape (WO 1996/021358; DSM 9660; e. g. Contans® WG, Intercept® WGfrom Bayer CropScience AG, Germany), harpin (alpha-beta) protein(Science 257, 85-88, 1992; e. g. Messenger™ or HARP-N-Tek from PlantHealth Care plc, U.K.), Helicoverpa armigera nucleopolyhedrovirus(HearNPV) (J. Invertebrate Pathol. 107, 112-126, 2011; e. g. Helicovex®from Adermatt Biocontrol, Switzerland; Diplomata® from Koppert, Brazil;Vivus® Max from AgBiTech Pty Ltd., Queensland, Australia), Helicoverpazea single capsid nucleopolyhedrovirus (HzSNPV) (e. g. Gemstar® fromCertis LLC, USA), Helicoverpa zea nucleopolyhedrovirus ABA-NPV-U (e. g.Heligen® from AgBiTech Pty Ltd., Queensland, Australia), Heterorhabditisbacteriophora (e. g. Nemasys® G from BASF Agricultural SpecialitiesLimited, UK), Isaria fumosorosea Apopka-97 isolated from mealy bug ongynura in Apopka, Fla., U.S.A. (ATCC 20874; Biocontrol Science Technol.22(7), 747-761, 2012; e. g. PFR97™ or PreFeRal® from Certis LLC, USA),Metarhizium anisopliae var. anisopliae F52 also called 275 or V275isolated from codling moth in Austria (DSM 3884, ATCC 90448; e. g.Met52® Novozymes Biologicals BioAg Group, Canada), Metschnikowiafructicola 277 isolated from grapes in the central part of Israel (U.S.Pat. No. 6,994,849; NRRL Y-30752; e. g. formerly Shemer® from Agrogreen,Israel), Paecilomyces ilacinus 251 isolated from infected nematode eggsin the Philippines (AGAL 89/030550; WO1991/02051; Crop Protection 27,352-361, 2008; e. g. BioAct® from Bayer CropScience AG, Germany andMeloCon® from Certis, USA), Pasteuria nishizawae Pn1 isolated from asoybean field in the mid-2000s in Illinois, U.S.A. (ATCC SD-5833;Federal Register 76(22), 5808, Feb. 2, 2011; e.g. Clariva™ PN fromSyngenta Crop Protection, LLC, USA), Penicillium bilaiae (also called P.bilail) strains ATCC 18309 (=ATCC 74319), ATCC 20851 and/or ATCC 22348(=ATCC 74318) originally isolated from soil in Alberta, Canada(Fertilizer Res. 39, 97-103, 1994; Can. J. Plant Sci. 78(1), 91-102,1998; U.S. Pat. No. 5,026,417, WO 1995/017806; e. g. Jump Start®,Provide® from Novozymes Biologicals BioAg Group, Canada), Reynoutriasachalinensis extract (EP 0307510 B1; e. g. Regalia® SC from MarroneBioInnovations, Davis, Calif., USA or Milsana® from BioFa AG, Germany),Steinernema carpocapsae (e. g. Millenium® from BASF AgriculturalSpecialities Limited, UK), S. feltiae (e. g. Nemashield® from BioWorks,Inc., USA; Nemasys® from BASF Agricultural Specialities Limited, UK),Streptomyces microflavus NRRL B-50550 (WO 2014/124369; BayerCropScience, Germany), T. harzianum T-22 also called KRL-AG2 (ATCC20847; BioControl 57, 687-696, 2012; e. g. Plantshield® from BioWorksInc., USA or SabrEx™ from Advanced Biological Marketing Inc., Van Wert,Ohio, USA).

According to the invention, the solid material (dry matter) of thebiopesticides (with the exception of oils such as Neem oil) areconsidered as active components (e.g. to be obtained after drying orevaporation of the extraction or suspension medium in case of liquidformulations of the microbial pesticides).

In accordance with the present invention, the weight ratios andpercentages used herein for a biological extract such as Quillay extractare based on the total weight of the dry content (solid material) of therespective extract(s).

The total weight ratios of compositions comprising at least onemicrobial pesticide in the form of viable microbial cells includingdormant forms, can be determined using the amount of CFU of therespective microorganism to calculate the total weight of the respectiveactive component with the following equation that 1×10¹⁰ CFU equals onegram of total weight of the respective active component. Colony formingunit is measure of viable microbial cells, in particular fungal andbacterial cells. In addition, here “CFU” may also be understood as thenumber of (juvenile) individual nematodes in case of (entomopathogenic)nematode biopesticides, such as Steinernema feltiae.

When mixtures comprising microbial pesticides are employed in cropprotection, the application rates preferably range from about 1×106 to5×1015 (or more) CFU/ha, preferably from about 1×108 to about 1×1013CFU/ha, and even more preferably from about 1×109 to about 1×1012CFU/ha. In the case of (entomopathogenic) nematodes as microbialpesticides (e. g. Steinernema feltiae), the application rates preferablyrange inform about 1×105 to 1×1012 (or more), more preferably from 1×108to 1×1011, even more preferably from 5×108 to 1×1010 individuals (e. g.in the form of eggs, juvenile or any other live stages, preferably in aninfective juvenile stage) per ha.

When mixtures comprising microbial pesticides are employed in seedtreatment, the application rates with respect to plant propagationmaterial preferably range from about 1×106 to 1×1012 (or more) CFU/seed.Preferably, the concentration is about 1×106 to about 1×109 CFU/seed. Inthe case of the microbial pesticides II, the application rates withrespect to plant propagation material also preferably range from about1×107 to 1×1014 (or more) CFU per 100 kg of seed, preferably from 1×109to about 1×1012 CFU per 100 kg of seed.

Formulations

The invention also relates to agrochemical compositions comprising anauxiliary and at least one compound of the present invention or amixture thereof.

An agrochemical composition comprises a pesticidally effective amount ofa compound of the present invention or a mixture thereof. The term“pesticidally effective amount” is defined below.

The compounds of the present invention or the mixtures thereof can beconverted into customary types of agro-chemical compositions, e. g.solutions, emulsions, suspensions, dusts, powders, pastes, granules,pressings, capsules, and mixtures thereof. Examples for compositiontypes are suspensions (e.g. SC, OD, FS), emulsifiable concentrates (e.g.EC), emulsions (e.g. EW, EO, ES, ME), capsules (e.g. CS, ZC), pastes,pastilles, wettable powders or dusts (e.g. WP, SP, WS, DP, DS),pressings (e.g. BR, TB, DT), granules (e.g. WG, SG, GR, FG, GG, MG),insecticidal articles (e.g. LN), as well as gel formulations for thetreatment of plant propagation materials such as seeds (e.g. GF). Theseand further compositions types are defined in the “Catalogue ofpesticide formulation types and international coding system”, TechnicalMono-graph No. 2, 6th Ed. May 2008, CropLife International.

The compositions are prepared in a known manner, such as described byMollet and Grubemann, Formulation technology, Wiley VCH, Weinheim, 2001;or Knowles, New developments in crop protection product formulation, Agrow Reports DS243, T&F Informa, London, 2005.

Examples for suitable auxiliaries are solvents, liquid carriers, solidcarriers or fillers, surfactants, dispersants, emulsifiers, wetters,adjuvants, solubilizers, penetration enhancers, protec-tive colloids,adhesion agents, thickeners, humectants, repellents, attractants,feeding stimu-lants, compatibilizers, bactericides, anti-freezingagents, anti-foaming agents, colorants, tackifi-ers and binders.

Suitable solvents and liquid carriers are water and organic solvents,such as mineral oil fractions of medium to high boiling point, e.g.kerosene, diesel oil; oils of vegetable or animal origin; aliphatic,cyclic and aromatic hydrocarbons, e. g. toluene, paraffin,tetrahydronaphthalene, al-kylated naphthalenes; alcohols, e.g. ethanol,propanol, butanol, benzylalcohol, cyclo¬hexanol; glycols; DMSO; ketones,e.g. cyclohexanone; esters, e.g. lactates, carbonates, fatty acidesters, gamma-butyrolactone; fatty acids; phosphonates; amines; amides,e.g. N-methylpyrrolidone, fatty acid dimethylamides; and mixturesthereof.

Suitable solid carriers or fillers are mineral earths, e.g. silicates,silica gels, talc, kaolins, limestone, lime, chalk, clays, dolomite,diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate,magnesium oxide; polysaccharide powders, e.g. cellulose, starch;fertilizers, e.g. ammonium sulfate, ammonium phosphate, ammoniumnitrate, ureas; products of vegetable origin, e.g. cereal meal, treebark meal, wood meal, nutshell meal, and mixtures thereof.

Suitable surfactants are surface-active compounds, such as anionic,cationic, nonionic and amphoteric surfactants, block polymers,polyelectrolytes, and mixtures thereof. Such surfactants can be used asemusifier, dispersant, solubilizer, wetter, penetration enhancer,protective colloid, or adjuvant. Examples of surfactants are listed inMcCutcheon's, Voll: Emulsifiers & Detergents, McCutcheon's Directories,Glen Rock, USA, 2008 (International Ed. or North American Ed.).

Suitable anionic surfactants are alkali, alkaline earth or ammoniumsalts of sulfonates, sulfates, phosphates, carboxylates, and mixturesthereof. Examples of sulfonates are alkylaryl-sulfonates,diphenylsulfonates, alpha-olefin sulfonates, lignine sulfonates,sulfonates of fatty acids and oils, sulfonates of ethoxylatedalkylphenols, sulfonates of alkoxylated arylphenols, sulfonates ofcondensed naphthalenes, sulfonates of dodecyl- and tridecylbenzenes,sulfonates of naphthalenes and alkyl naphthalenes, sulfosuccinates orsulfosuccinamates. Examples of sulfates are sulfates of fatty acids andoils, of ethoxylated alkylphenols, of alcohols, of ethox-ylatedalcohols, or of fatty acid esters. Examples of phosphates are phosphateesters. Exam-pies of carboxylates are alkyl carboxylates, andcarboxylated alcohol or alkylphenol eth-ovlates.

Suitable nonionic surfactants are alkoxylates, N-subsituted fatty acidamides, amine oxides, esters, sugar-based surfactants, polymericsurfactants, and mixtures thereof. Examples of alkoxylates are compoundssuch as alcohols, alkylphenols, amines, amides, arylphenols, fatty acidsor fatty acid esters which have been alkoxylated with 1 to 50equivalents. Ethylene oxide and/or propylene oxide may be employed forthe alkoxylation, preferably ethylene oxide. Exam-pies of N-substitutedfatty acid amides are fatty acid glucamides or fatty acid alkanolamides.Examples of esters are fatty acid esters, glycerol esters ormonoglycerides. Examples of sugar-based surfactants are sorbitans,ethoxylated sorbitans, sucrose and glucose esters oralkylpolyglucosides. Examples of polymeric surfactants are homo- orcopolymers of vinylpyrrolidone, vinylalcohols, or vinylacetate.

Suitable cationic surfactants are quaternary surfactants, for examplequaternary ammonium compounds with one or two hydrophobic groups, orsalts of long-chain primary amines. Suitable amphoteric surfactants arealkylbetains and imidazolines. Suitable block polymers are blockpolymers of the A-B or A-B-A type comprising blocks of polyethyleneoxide and polypropylene oxide, or of the A-B-C type comprising alkanol,polyethylene oxide and polypropylene oxide. Suitable polyelectrolytesare polyacids or polybases. Examples of polyacids are alkali salts ofpolyacrylic acid or polyacid comb polymers. Examples of polybases arepolyvinylamines or polyethyleneamines.

Suitable adjuvants are compounds, which have a neglectable or even nopesticidal activity themselves, and which improve the biologicalperformance of the compounds of the present invention on the target.Examples are surfactants, mineral or vegetable oils, and otherauxilaries. Further examples are listed by Knowles, Adjuvants andadditives, Agrow Reports DS256, T&F Informa UK, 2006, chapter 5.

Suitable thickeners are polysaccharides (e.g. xanthan gum,carboxymethylcellulose), anorganic clays (organically modified orunmodified), polycarboxylates, and silicates.

Suitable bactericides are bronopol and isothiazolinone derivatives suchas alkylisothiazoli-nones and benzisothiazolinones.

Suitable anti-freezing agents are ethylene glycol, propylene glycol,urea and glycerin.

Suitable anti-foaming agents are silicones, long chain alcohols, andsalts of fatty acids.

Suitable colorants (e.g. in red, blue, or green) are pigments of lowwater solubility and water-soluble dyes. Examples are inorganiccolorants (e.g. iron oxide, titan oxide, iron hexacyanoferrate) andorganic colorants (e.g. alizarin-, azo- and phthalocyanine colorants).

Suitable tackifiers or binders are polyvinylpyrrolidons,polyvinylacetates, polyvinyl alcohols, polyacrylates, biological orsynthetic waxes, and cellulose ethers.

Examples for composition types and their preparation are:

i) Water-Soluble Concentrates (SL, LS)

10-60 wt % of a compound I according to the invention and 5-15 wt %wetting agent (e.g. alcohol alkoxylates) are dissolved in water and/orin a water-soluble solvent (e.g. alcohols) up to 100 wt %. The activesubstance dissolves upon dilution with water.

ii) Dispersible Concentrates (DC)

5-25 wt % of a compound I according to the invention and 1-10 wt %dispersant (e. g. polyvinylpyrrolidone) are dissolved in up to 100 wt %organic solvent (e.g. cyclohexanone). Dilution with water gives adispersion.

iii) Emulsifiable Concentrates (EC)

15-70 wt % of a compound I according to the invention and 5-10 wt %emulsifiers (e.g. calcium dodecylbenzenesulfonate and castor oilethoxylate) are dissolved in up to 100 wt % water-insoluble organicsolvent (e.g. aromatic hydrocarbon). Dilution with water gives anemulsion.

iv) Emulsions (EW, EO, ES)

5-40 wt % of a compound I according to the invention and 1-10 wt %emulsifiers (e.g. calcium dodecylbenzenesulfonate and castor oilethoxylate) are dissolved in 20-40 wt % water-insoluble organic solvent(e.g. aromatic hydrocarbon). This mixture is introduced into up to 100wt % water by means of an emulsifying machine and made into ahomogeneous emulsion. Dilution with water gives an emulsion.

v) Suspensions (SC, OD, FS)

In an agitated ball mill, 20-60 wt % of a compound I according to theinvention are comminuted with addition of 2-10 wt % dispersants andwetting agents (e.g. sodium lignosulfonate and alcohol ethoxylate),0.1-2 wt % thickener (e.g. xanthan gum) and up to 100 wt % water to givea fine active substance suspension. Dilution with water gives a stablesuspension of the active sub-stance. For FS type composition up to 40 wt% binder (e.g. polyvinylalcohol) is added.

vi) Water-Dispersible Granules and Water-Soluble Granules (WG, SG)

50-80 wt % of a compound I according to the invention are ground finelywith addition of up to 100 wt % dispersants and wetting agents (e.g.sodium lignosulfonate and alcohol ethoxylate) and prepared aswater-dispersible or water-soluble granules by means of technicalappliances (e. g. extrusion, spray tower, fluidized bed). Dilution withwater gives a stable dispersion or solution of the active substance.

vii) Water-Dispersible Powders and Water-Soluble Powders (WP, SP, WS)

50-80 wt % of a compound I according to the invention are ground in arotor-stator mill with ad-dition of 1-5 wt % dispersants (e.g. sodiumlignosulfonate), 1-3 wt % wetting agents (e.g. alcohol ethoxylate) andup to 100 wt % solid carrier, e.g. silica gel. Dilution with water givesa stable dis-persion or solution of the active substance.

-   -   viii) Gel (GW, GF)

In an agitated ball mill, 5-25 wt % of a compound I according to theinvention are comminuted with addition of 3-10 wt % dispersants (e.g.sodium lignosulfonate), 1-5 wt % thickener (e.g. carboxymethylcellulose)and up to 100 wt % water to give a fine suspension of the activesub-stance. Dilution with water gives a stable suspension of the activesubstance.

ix) Microemulsion (ME)

5-20 wt % of a compound I according to the invention are added to 5-30wt % organic solvent blend (e.g. fatty acid dimethylamide andcyclohexanone), 10-25 wt % surfactant blend (e.g. alkohol ethoxylate andarylphenol ethoxylate), and water up to 100%. This mixture is stirredfor 1 h to produce spontaneously a thermodynamically stablemicroemulsion.

x) Microcapsules (CS)

An oil phase comprising 5-50 wt % of a compound I according to theinvention, 0-40 wt % water insoluble organic solvent (e.g. aromatichydrocarbon), 2-15 wt % acrylic monomers (e.g. methylmethacrylate,methacrylic acid and a di- or triacrylate) are dispersed into an aqueoussolution of a protective colloid (e.g. polyvinyl alcohol). Radicalpolymerization initiated by a radi-cal initiator results in theformation of poly(meth)acrylate microcapsules. Alternatively, an oilphase comprising 5-50 wt % of a compound I according to the invention,0-40 wt % water insolu-ble organic solvent (e.g. aromatic hydrocarbon),and an isocyanate monomer (e.g. diphenylme-thene-4,4′-diisocyanatae) aredispersed into an aqueous solution of a protective colloid (e.g.polyvinyl alcohol). The addition of a polyamine (e.g.hexamethylenediamine) results in the for-mation of a polyureamicrocapsule. The monomers amount to 1-10 wt %. The wt % relate to thetotal CS composition.

xi) Dustable Powders (DP, DS)

1-10 wt % of a compound I according to the invention are ground finelyand mixed intimately with up to 100 wt % solid carrier, e.g. finelydivided kaolin.

xii) Granules (GR, FG)

0.5-30 wt % of a compound I according to the invention is ground finelyand associated with up to 100 wt % solid carrier (e.g. silicate).Granulation is achieved by extrusion, spray-drying or the fluidized bed.

-   -   xiii) Ultra-Low Volume Liquids (UL)

1-50 wt % of a compound I according to the invention are dissolved in upto 100 wt % organic solvent, e.g. aromatic hydrocarbon.

The compositions types i) to xi) may optionally comprise furtherauxiliaries, such as 0.1-1 wt % bactericides, 5-15 wt % anti-freezingagents, 0.1-1 wt % anti-foaming agents, and 0.1-1 wt % colorants.

The agrochemical compositions generally comprise between 0.01 and 95%,preferably between 0.1 and 90%, and most preferably between 0.5 and 75%,by weight of active sub-stance. The active substances are employed in apurity of from 90% to 100%, preferably from 95% to 100% (according toNMR spectrum).

Various types of oils, wetters, adjuvants, fertilizer, ormicronutrients, and other pesticides (e.g. herbicides, insecticides,fungicides, growth regulators, safeners) may be added to the activesubstances or the compositions comprising them as premix or, ifappropriate not until immediately prior to use (tank mix). These agentscan be admixed with the compositions according to the invention in aweight ratio of 1:100 to 100:1, preferably 1:10 to 10:1.

The user applies the composition according to the invention usually froma predosage de-vice, a knapsack sprayer, a spray tank, a spray plane, oran irrigation system. Usually, the agrochemical composition is made upwith water, buffer, and/or further auxiliaries to the desiredapplication concentration and the ready-to-use spray liquor or theagrochemical composition according to the invention is thus obtained.Usually, 20 to 2000 liters, preferably 50 to 400 liters, of theready-to-use spray liquor are applied per hectare of agricultural usefularea.

According to one embodiment, individual components of the compositionaccording to the invention such as parts of a kit or parts of a binaryor ternary mixture may be mixed by the user himself in a spray tank andfurther auxiliaries may be added, if appropriate.

In a further embodiment, either individual components of the compositionaccording to the invention or partially premixed components, e. g.components comprising compounds of the present invention and/or mixingpartners as defined above, may be mixed by the user in a spray tank andfurther auxiliaries and additives may be added, if appropriate.

In a further embodiment, either individual components of the compositionaccording to the invention or partially premixed components, e. g.components comprising compounds of the present invention and/or mixingpartners as defined above, can be applied jointly (e.g. after tank mix)or consecutively.

Application Methods

The compounds of the present invention are suitable for use inprotecting crops, plants, plant propagation materials, such as seeds, orsoil or water, in which the plants are growing, from attack orinfestation by animal pests. Therefore, the present invention alsorelates to a plant protection method, which comprises contacting crops,plants, plant propagation materials, such as seeds, or soil or water, inwhich the plants are growing, to be protected from attack or infestationby animal pests, with a pesticidally effective amount of a compound ofthe present invention. The compounds of the present invention are alsosuitable for use in combating or controlling animal pests. Therefore,the present invention also relates to a method of combating orcontrolling animal pests, which comprises contacting the animal pests,their habitat, breeding ground, or food supply, or the crops, plants,plant propagation materials, such as seeds, or soil, or the area,material or environment in which the animal pests are growing or maygrow, with a pesticidally effective amount of a compound of the presentinvention.

The compounds of the present invention are effective through bothcontact and ingestion. Furthermore, the compounds of the presentinvention can be applied to any and all developmental stages, such asegg, larva, pupa, and adult.

The compounds of the present invention can be applied as such or in formof compositions comprising them as defined above. Furthermore, thecompounds of the present invention can be applied together with a mixingpartner as defined above or in form of compositions comprising saidmixtures as defined above. The components of said mixture can be appliedsimultaneously, jointly or separately, or in succession, that isimmediately one after another and thereby creating the mixture “in situ”on the desired location, e.g. the plant, the sequence, in the case ofseparate application, generally not having any effect on the result ofthe control measures.

The application can be carried out both before and after the infestationof the crops, plants, plant propagation materials, such as seeds, soil,or the area, material or environment by the pests.

Suitable application methods include inter alia soil treatment, seedtreatment, in furrow application, and foliar application. Soil treatmentmethods include drenching the soil, drip irrigation (drip applicationonto the soil), dipping roots, tubers or bulbs, or soil injection. Seedtreatment techniques include seed dressing, seed coating, seed dusting,seed soaking, and seed pelleting. In furrow applications typicallyinclude the steps of making a furrow in cultivated land, seeding thefurrow with seeds, applying the pesticidally active compound to thefurrow, and closing the furrow. Foliar application refers to theapplication of the pesticidally active compound to plant foliage, e.g.through spray equipment. For foliar applications, it can be advantageousto modify the behavior of the pests by use of pheromones in combinationwith the compounds of the present invention. Suitable pheromones forspecific crops and pests are known to a skilled person and publiclyavailable from databases of pheromones and semiochemicals, such ashttp://www.pherobase.com.

As used herein, the term “contacting” includes both direct contact(applying the compounds/compositions directly on the animal pest orplant—typically to the foliage, stem or roots of the plant) and indirectcontact (applying the compounds/compositions to the locus, i.e. habitat,breeding ground, plant, seed, soil, area, material or environment inwhich a pest is growing or may grow, of the animal pest or plant).

The term “animal pest” includes arthropods, gastropods, and nematodes.Preferred animal pests according to the invention are arthropods,preferably insects and arachnids, in particular insects. Insects, whichare of particular relevance for crops, are typically referred to as cropinsect pests.

The term “crop” refers to both, growing and harvested crops.

The term “plant” includes cereals, e.g. durum and other wheat, rye,barley, triticale, oats, rice, or maize (fodder maize and sugarmaize/sweet and field corn); beet, e.g. sugar beet or fodder beet;fruits, such as pomes, stone fruits or soft fruits, e.g. apples, pears,plums, peaches, nectarines, almonds, cherries, papayas, strawberries,raspberries, blackberries or gooseberries; leguminous plants, such asbeans, lentils, peas, alfalfa or soybeans; oil plants, such as rapeseed(oilseed rape), turnip rape, mustard, olives, sunflowers, coconut, cocoabeans, castor oil plants, oil palms, ground nuts or soybeans; cucurbits,such as squashes, pumpkins, cucumber or melons; fiber plants, such ascotton, flax, hemp or jute; citrus fruit, such as oranges, lemons,grapefruits or mandarins; vegetables, such as eggplant, spinach, lettuce(e.g. iceberg lettuce), chicory, cabbage, asparagus, cabbages, carrots,onions, garlic, leeks, tomatoes, potatoes, cucurbits or sweet peppers;lauraceous plants, such as avocados, cinnamon or camphor; energy and rawmaterial plants, such as corn, soybean, rapeseed, sugar cane or oilpalm; tobacco; nuts, e.g. walnuts; pistachios; coffee; tea; bananas;vines (table grapes and grape juice grape vines); hop; sweet leaf (alsocalled Stevia); natural rubber plants or ornamental and forestry plants,such as flowers (e.g. carnation, petunias, geranium/pelargoniums,pansies and impatiens), shrubs, broad-leaved trees (e.g. poplar) orevergreens, e.g. conifers; eucalyptus; turf; lawn; grass such as grassfor animal feed or ornamental uses. Preferred plants include potatoessugar beets, tobacco, wheat, rye, barley, oats, rice, corn, cotton,soybeans, rapeseed, legumes, sunflowers, coffee or sugar cane; fruits;vines; ornamentals; or vegetables, such as cucumbers, tomatoes, beans orsquashes.

The term “plant” is to be understood as including wild type plants andplants, which have been modified by either conventional breeding, ormutagenesis or genetic engineering, or by a combination thereof.

Plants, which have been modified by mutagenesis or genetic engineering,and are of particular commercial importance, include alfalfa, rapeseed(e.g. oilseed rape), bean, carnation, chicory, cotton, eggplant,eucalyptus, flax, lentil, maize, melon, papaya, petunia, plum, poplar,potato, rice, soybean, squash, sugar beet, sugarcane, sunflower, sweetpepper, tobacco, tomato, and cereals (e.g. wheat), in particular maize,soybean, cotton, wheat, and rice. In plants, which have been modified bymutagenesis or genetic engineering, one or more genes have beenmutagenized or integrated into the genetic material of the plant. Theone or more mutagenized or integrated genes are preferably selected frompat, epsps, cry1Ab, bar, cry1Fa2, cry1Ac, cry34Ab1, cry35AB1, cry3A,cryF, cry1F, mcry3a, cry2Ab2, cry3Bb1, cry1A.105, dfr, barnase,vip3Aa20, barstar, als, bxn, bp40, asn1, and ppo5. The mutagenesis orintegration of the one or more genes is performed in order to improvecertain properties of the plant. Such properties, also known as traits,include abiotic stress tolerance, altered growth/yield, diseaseresistance, herbicide tolerance, insect resistance, modified productquality, and pollination control. Of these properties, herbicidetolerance, e.g. imidazolinone tolerance, glyphosate tolerance, orglufosinate tolerance, is of particular importance. Several plants havebeen rendered tolerant to herbicides by mutagenesis, for exampleClearfield® oilseed rape being tolerant to imidazolinones, e.g.imazamox. Alternatively, genetic engineering methods have been used torender plants, such as soybean, cotton, corn, beets and oil seed rape,tolerant to herbicides, such as glyphosate and glufosinate, some ofwhich are commercially available under the trade names RoundupReady®(glyphosate) and LibertyLink® (glufosinate). Furthermore, insectresistance is of importance, in particular lepidopteran insectresistance and coleopteran insect resistance. Insect resistance istypically achieved by modifying plants by integrating cry and/or vipgenes, which were isolated from Bacillus thuringiensis (Bt), and codefor the respective Bt toxins. Genetically modified plants with insectresistance are commercially available under trade names includingWideStrike®, Bollgard®, Agrisure®, Herculex®, YieldGard®, Genuity®, andIntacta®. Plants may be modified by mutagenesis or genetic engineeringeither in terms of one property (singular traits) or in terms of acombination of properties (stacked traits). Stacked traits, e.g. thecombination of herbicide tolerance and insect resistance, are ofincreasing importance. In general, all relevant modified plants inconnection with singular or stacked traits as well as detailedinformation as to the mutagenized or integrated genes and the respectiveevents are available from websites of the organizations “InternationalService for the Acquisition of Agri-biotech Applications (ISAAA)”(http://www.isaaa.org/gmap-provaldatabase) and “Center for EnvironmentalRisk Assessment (CERA)” (http://cera-gmc.org/GMCropDatabase).

It has surprisingly been found that the pesticidal activity of thecompounds of the present invention may be enhanced by the insecticidaltrait of a modified plant. Furthermore, it has been found that thecompounds of the present invention are suitable for preventing insectsto become resistant to the insecticidal trait or for combating pests,which already have become resistant to the insecticidal trait of amodified plant. Moreover, the compounds of the present invention aresuitable for combating pests, against which the insecticidal trait isnot effective, so that a complementary insecticidal activity canadvantageously be used.

The term “plant propagation material” refers to all the generative partsof the plant such as seeds and vegetative plant material such ascuttings and tubers (e.g. potatoes), which can be used for themultiplication of the plant. This includes seeds, roots, fruits, tubers,bulbs, rhizomes, shoots, sprouts and other parts of plants. Seedlingsand young plants, which are to be transplanted after germination orafter emergence from soil, may also be included. These plant propagationmaterials may be treated prophylactically with a plant protectioncompound either at or before planting or transplanting.

The term “seed” embraces seeds and plant propagules of all kindsincluding but not limited to true seeds, seed pieces, suckers, corms,bulbs, fruit, tubers, grains, cuttings, cut shoots and the like, andmeans in a preferred embodiment true seeds.

In general, “pesticidally effective amount” means the amount of activeingredient needed to achieve an observable effect on growth, includingthe effects of necrosis, death, retardation, prevention, and removal,destruction, or otherwise diminishing the occurrence and activity of thetarget organism. The pesticidally effective amount can vary for thevarious compounds/compositions used in the invention. A pesticidallyeffective amount of the compositions will also vary according to theprevailing conditions such as desired pesticidal effect and duration,weather, target species, locus, mode of application, and the like.

In the case of soil treatment, in furrow application or of applicationto the pests dwelling place or nest, the quantity of active ingredientranges from 0.0001 to 500 g per 100 m², preferably from 0.001 to 20 gper 100 m².

For use in treating crop plants, e.g. by foliar application, the rate ofapplication of the active ingredients of this invention may be in therange of 0.0001 g to 4000 g per hectare, e.g. from 1 g to 2 kg perhectare or from 1 g to 750 g per hectare, desirably from 1 g to 100 gper hectare, more desirably from 10 g to 50 g per hectare, e.g., 10 to20 g per hectare, 20 to 30 g per hectare, 30 to 40 g per hectare, or 40to 50 g per hectare.

The compounds of the present invention are particularly suitable for usein the treatment of seeds in order to protect the seeds from insectpests, in particular from soil-living insect pests, and the resultingseedling's roots and shoots against soil pests and foliar insects. Thepresent invention therefore also relates to a method for the protectionof seeds from insects, in particular from soil insects, and of theseedling's roots and shoots from insects, in particular from soil andfoliar insects, said method comprising treating the seeds before sowingand/or after pre-germination with a compound of the present invention.The protection of the seedling's roots and shoots is preferred. Morepreferred is the protection of seedling's shoots from piercing andsucking insects, chewing insects and nematodes.

The term “seed treatment” comprises all suitable seed treatmenttechniques known in the art, such as seed dressing, seed coating, seeddusting, seed soaking, seed pelleting, and in-furrow applicationmethods. Preferably, the seed treatment application of the activecompound is carried out by spraying or by dusting the seeds beforesowing of the plants and before emergence of the plants.

The present invention also comprises seeds coated with or containing theactive compound. The term coated with and/or containing generallysignifies that the active ingredient is for the most part on the surfaceof the propagation product at the time of application, although agreater or lesser part of the ingredient may penetrate into thepropagation product, depending on the method of application. When thesaid propagation product is (re)planted, it may absorb the activeingredient.

Suitable seed is for example seed of cereals, root crops, oil crops,vegetables, spices, ornamentals, for example seed of durum and otherwheat, barley, oats, rye, maize (fodder maize and sugar maize/sweet andfield corn), soybeans, oil crops, crucifers, cotton, sunflowers,bananas, rice, oilseed rape, turnip rape, sugarbeet, fodder beet,eggplants, potatoes, grass, lawn, turf, fodder grass, tomatoes, leeks,pumpkin/squash, cabbage, iceberg lettuce, pepper, cucumbers, melons,Brassica species, melons, beans, peas, garlic, onions, carrots, tuberousplants such as potatoes, sugar cane, tobacco, grapes, petunias,geranium/pelargoniums, pansies and impatiens.

In addition, the active compound may also be used for the treatment ofseeds from plants, which have been modified by mutagenisis or geneticengineering, and which e.g. tolerate the action of herbicides orfungicides or insecticides. Such modified plants have been described indetail above.

Conventional seed treatment formulations include for example flowableconcentrates FS, solutions LS, suspoemulsions (SE), powders for drytreatment DS, water dispersible powders for slurry treatment WS,water-soluble powders SS and emulsion ES and EC and gel formulation GF.These formulations can be applied to the seed diluted or undiluted.Application to the seeds is carried out before sowing, either directlyon the seeds or after having pregerminated the latter. Preferably, theformulations are applied such that germination is not included.

The active substance concentrations in ready-to-use formulations, whichmay be obtained after two-to-tenfold dilution, are preferably from 0.01to 60% by weight, more preferably from 0.1 to 40% by weight.

In a preferred embodiment a FS formulation is used for seed treatment.Typically, a FS formulation may comprise 1-800 g/l of active ingredient,1-200 g/l Surfactant, 0 to 200 g/l antifreezing agent, 0 to 400 g/l ofbinder, 0 to 200 g/l of a pigment and up to 1 liter of a solvent,preferably water.

Especially preferred FS formulations of the compounds of the presentinvention for seed treatment usually comprise from 0.1 to 80% by weight(1 to 800 g/l) of the active ingredient, from 0.1 to 20% by weight (1 to200 g/l) of at least one surfactant, e.g. 0.05 to 5% by weight of awetter and from 0.5 to 15% by weight of a dispersing agent, up to 20% byweight, e.g. from 5 to 20% of an anti-freeze agent, from 0 to 15% byweight, e.g. 1 to 15% by weight of a pigment and/or a dye, from 0 to 40%by weight, e.g. 1 to 40% by weight of a binder (sticker/adhesion agent),optionally up to 5% by weight, e.g. from 0.1 to 5% by weight of athickener, optionally from 0.1 to 2% of an anti-foam agent, andoptionally a preservative such as a biocide, antioxidant or the like,e.g. in an amount from 0.01 to 1% by weight and a filler/vehicle up to100% by weight.

In the treatment of seed, the application rates of the compounds of theinvention are generally from 0.1 g to 10 kg per 100 kg of seed,preferably from 1 g to 5 kg per 100 kg of seed, more preferably from 1 gto 1000 g per 100 kg of seed and in particular from 1 g to 200 g per 100kg of seed, e.g. from 1 g to 100 g or from 5 g to 100 g per 100 kg ofseed.

The invention therefore also relates to seed comprising a compound ofthe present invention, or an agriculturally useful salt thereof, asdefined herein. The amount of the compound of the present invention orthe agriculturally useful salt thereof will in general vary from 0.1 gto 10 kg per 100 kg of seed, preferably from 1 g to 5 kg per 100 kg ofseed, in particular from 1 g to 1000 g per 100 kg of seed. For specificcrops such as lettuce the rate can be higher.

The compounds of the present invention may also be used for improvingthe health of a plant. Therefore, the present invention also relates toa method for improving plant health by treating a plant, plantpropagation material and/or the locus where the plant is growing or isto grow with an effective and non-phytotoxic amount of a compound of thepresent invention.

As used herein “an effective and non-phytotoxic amount” means that thecompound is used in a quantity which allows to obtain the desired effectbut which does not give rise to any phytotoxic symptom on the treatedplant or on the plant grown from the treated propagule or treated soil.

The terms “plant” and “plant propagation material” are defined above.

“Plant health” is defined as a condition of the plant and/or itsproducts which is determined by several aspects alone or in combinationwith each other such as yield (for example increased biomass and/orincreased content of valuable ingredients), quality (for exampleimproved content or composition of certain ingredients or shelf life),plant vigour (for example improved plant growth and/or greener leaves(“greening effect”), tolerance to abiotic (for example drought) and/orbiotic stress (for example disease) and production efficiency (forexample, harvesting efficiency, processability).

The above identified indicators for the health condition of a plant maybe interdependent and may result from each other. Each indicator isdefined in the art and can be determined by methods known to a skilledperson.

The compounds of the invention are also suitable for use againstnon-crop insect pests. For use against said non-crop pests, compounds ofthe present invention can be used as bait composition, gel, generalinsect spray, aerosol, as ultra-low volume application and bed net(impregnated or surface applied). Furthermore, drenching and roddingmethods can be used.

As used herein, the term “non-crop insect pest” refers to pests, whichare particularly relevant for non-crop targets, such as ants, termites,wasps, flies, ticks, mosquitos, crickets, or cockroaches.

The bait can be a liquid, a solid or a semisolid preparation (e.g. agel). The bait employed in the composition is a product, which issufficiently attractive to incite insects such as ants, termites, wasps,flies, mosquitos, crickets etc. or cockroaches to eat it. Theattractiveness can be manipulated by using feeding stimulants or sexpheromones. Food stimulants are chosen, for example, but notexclusively, from animal and/or plant proteins (meat-, fish- or bloodmeal, insect parts, egg yolk), from fats and oils of animal and/or plantorigin, or mono-, oligo- or polyorganosaccharides, especially fromsucrose, lactose, fructose, dextrose, glucose, starch, pectin or evenmolasses or honey. Fresh or decaying parts of fruits, crops, plants,animals, insects or specific parts thereof can also serve as a feedingstimulant. Sex pheromones are known to be more insect specific. Specificpheromones are described in the literature (e.g.http://www.pherobase.com), and are known to those skilled in the art.

For use in bait compositions, the typical content of active ingredientis from 0.001 weight % to 15 weight %, desirably from 0.001 weight % to5% weight % of active compound.

Formulations of the compounds of the present invention as aerosols (e.gin spray cans), oil sprays or pump sprays are highly suitable for thenon-professional user for controlling pests such as flies, fleas, ticks,mosquitos or cockroaches. Aerosol recipes are preferably composed of theactive compound, solvents, furthermore auxiliaries such as emulsifiers,perfume oils, if appropriate stabilizers, and, if required, propellants.

The oil spray formulations differ from the aerosol recipes in that nopropellants are used.

For use in spray compositions, the content of active ingredient is from0.001 to 80 weights %, preferably from 0.01 to 50 weight % and mostpreferably from 0.01 to 15 weight %.

The compounds of the present invention and its respective compositionscan also be used in mosquito and fumigating coils, smoke cartridges,vaporizer plates or long-term vaporizers and also in moth papers, mothpads or other heat-independent vaporizer systems.

Methods to control infectious diseases transmitted by insects (e.g.malaria, dengue and yellow fever, lymphatic filariasis, andleishmaniasis) with compounds of the present invention and itsrespective compositions also comprise treating surfaces of huts andhouses, air spraying and impregnation of curtains, tents, clothingitems, bed nets, tsetse-fly trap or the like. Insecticidal compositionsfor application to fibers, fabric, knitgoods, nonwovens, nettingmaterial or foils and tarpaulins preferably comprise a mixture includingthe insecticide, optionally a repellent and at least one binder.

The compounds of the present invention and its compositions can be usedfor protecting wooden materials such as trees, board fences, sleepers,frames, artistic artifacts, etc. and buildings, but also constructionmaterials, furniture, leathers, fibers, vinyl articles, electric wiresand cables etc. from ants and/or termites, and for controlling ants andtermites from doing harm to crops or human being (e.g. when the pestsinvade into houses and public facilities).

Customary application rates in the protection of materials are, forexample, from 0.001 g to 2000 g or from 0.01 g to 1000 g of activecompound per m² treated material, desirably from 0.1 g to 50 g per m².

Insecticidal compositions for use in the impregnation of materialstypically contain from 0.001 to 95 weight %, preferably from 0.1 to 45weight %, and more preferably from 1 to 25 weight % of at least onerepellent and/or insecticide.

Pests

The compounds of the present invention are especially suitable forefficiently combating animal pests such as arthropods, gastropods andnematodes including but not limited to:

insects from the order of Lepidoptera, for example Achroia grisella,Acleris spp. such as A. fimbriana, A. gloverana, A. variana;Acroleplopsis assectella, Acronicta major, Adoxophyes spp. such as A.cyrtosema, A. orana; Aedia leucomelas, Agrotis spp. such as A.exclamationis; A. fucosa, A. ipsilon, A. orthogoma, A. segetum, A.subterranea; Alabama argillacea, Aleurodicus dispersus, Alsophilapometana, Ampelophaga rublginosa, Amyelois transitella, Anacampsissarcitella, Anagasta kuehniella, Anarsia lineatella, Anisota senatoria,Antheraea pernyi, Anticarsla (=Thermesia) spp. such as A. gemmatalisAparnea spp., Aproaerema modicella, Archips spp. such as A. argyrospila,A. fuscocupreanus, A. rosana, A. xyloseanus; Argyresthia conjugella,Argyroploce spp., Argyrotaenia spp. such as A. velutinana; Athetisminclara, Austroasca vindignsea, Autographa gamma, Autographa nignsigna,Barathra brassicae, spp., Bonagota salubncola, Borbo cinnara,Bucculatrix thurberiella, Bupalus piniarius, Busseola spp., Cacoeciaspp. such as C. murinana, C. podana; Cactoblastis cactorum, Cadracautella, Calingo brazillensis, Caloptilis theivora, Capua reticulana,Carposina spp. such as C. niponensis; C. sasakii; Cephus spp.,Chaetocnema aridula, Cheimatobia brumata, Chilo spp. such as C. indicus,C. suppressalis, C. partellus; Choreutis pariana, Choristoneura spp.such as C. conflictana, C. fumiferana, C. longicellana, C. murinana, C.occidentalis, C. rosaceana; Chlysodeixis (=Pseucloplusia) spp. such asC. eriosoma, C. includens; Cirphis unipuncta, Clysla ambiguella,Cnaphalocerus spp., Cnaphalocrocis medinalis; Cnephasia spp., Cochyllshospes, Coleophora spp., Colias eurytheme, Conopomorpha spp.,Conotrachelus spp., Copitarsia spp., Corcyra cephalonica, Crambuscaliginosellus, Crambus teterrellus, Crocidosema (=Epinotia) aporema,Cydalima (=Diaphania) perspectalis; Cydia (=Carpocapsa) spp. such as C.pomonella, C. latiferreana; Dalaca noctuides, Datana integerrima,Dasychira pinicola, Dendrolimus spp. such as D. pini; D. spectabills; D.sibiricus; Desmia funeralis, Diaphania spp. such as D. nitidalis; D.hyalinata; Diatraea grandlosella, Diatraea saccharalis; DiphtheraFestiva, Earias spp. such as E. insulana, E. vittella; Ecdytolophaaurantianu, (=Xylomyges) curialis; Elasmopalpus lignosellus, Eldanasaccharina, Enclopiza viteana, Ennomos subsignana, Eoreuma loftini,Ephestia spp. such as E. cautella, E. elutella, E. kuehniella; Epinotiaaporema, Epiphyas postvittana, Erannis tillaria, Erionota thrax, Etiellaspp., Eulla spp., Eupoecilla ambiguella, Euproctis chlysorrhoea, Euxoaspp., Evetria boullana, Faronta albilinea, Feltia spp. such as F.subterranean; Galleria mellonella, Gracillaria spp., Grapholita spp.such as G. funebrana, G. molesta, G. inopinata; Halysidota spp.,Harrisina americana, Hedylepta spp., Helicoverpa spp. such as H.armigera (=Heliothis armigera), H. zea (=Heiliothis zea); Heiliothisspp. such as H. assulta, H. subflexa, H. virescens Hellula spp. such asH. undalis; H. rogatalis; Helocoverpa gelotopoeon, Hemlleuca oliviae,Herpetogramma licarsisalis; Hibernia defoliaria, Hofmannophilapseudospretella, Homoeosoma electellum, Homona magnanima, Hypena scabra,Hyphantria cunea, Hyponomeuta padella, Hyponomeuta malinellus, Kakivoriaflavofasciata, Keiferialycopersicella, Lambdina fiscellaria fiscellaria,Lambdina fiscellaria lugubrosa, Lamprosema indicata, Laspeyresiamolesta, Leguminivora glycinivorella, Lerodea eufala, Leucinodesorbonalis; Leucoma salicis; Leucoptera spp. such as L. coffeella, L.scitella; Leuminivora lycinivorella, Lithocolletis blancardella,Lithophane antennata, Llattla octo (=Amyna axis), Lobesia botrana,Lophocampa spp., Loxagrotis albicosta, Loxostege spp. such as L.sticticalis; L. cereralis Lymantria spp. such as L. dispar, L. monacha;Lyonetia clerkella, Lyonetia prunifoliella, Malacosoma spp. such as M.americanum, M. californIcum, M. constrictum, M. neustria; Mamestra spp.such as M. brassicae, M. configurata; Mamstra brassicae, Manduca spp.such as M. quinquemaculata, M. sexta; Marasmia spp, Marmara spp., Marucatestulalis; Megalopyge lanata, Melanchra picta, Melanitis leda, Mocisspp. such as M. lapites, M. repanda; Mocis latipes, Monochroa fragariae,Mythimna separata, Nemapogon cloacella, Neoleucinodes elegantalis;Nepytia spp., Nymphula spp., Olketicus spp., Omiodes indicata, Omphisaanastomosalis; Operophtera brumata, Orgyia pseudotsugata, Oria spp.,Orthaga thyrisalis; OstrInia spp. such as O. nubilalis Oulema oryzae,Paleacrita vernata, Panolis flammea, Parnara spp., Papaipema nebris,Papilio cresphontes, Paramyelois transltella, Paranthrene regalis,Paysandisia archon, Pectinophora spp. such as P. gossypiella; Peridromasaucia, Perileucoptera spp., such as P. coffeella; Phalera bucephala,Phryganidia californica, Phthorimaea spp. such as P. operculella;Phyllocnistis citrella, Phyllonorycter spp. such as P. blancardella, P.crataegella, P. issikii, P. ringoniella; Pieris spp. such as P.brassicae, P. rapae, P. napi; Pilocrocis tripunctata, Plathypena scabra,Platynota spp. such as P. flavedana, P. idaeusalis; P. stultana;Platyptilia carduidactyla, Plebejus argus, Plodia interpunctella, Plusiaspp, Plutella maculipennis Plutella xylostella, Pontia protodica, Praysspp., Prodenia spp., Proxenus lepigone, Pseudaletia spp. such as P.sequax, P. unlpuncta; Pyrausta nubllalis; Rachlplusla nu, Richiaalbicosta, Rhizobius ventralis, Rhyaclonia frustrana, Sabulodesaegrotata, Schizura concinna, Schoenobius spp., Schreckenstelniafestaliella, Scirpophaga spp. such as S. incertulas, S. innotata; Scotiasegetum, Sesamia spp. such as S. inferens, Seudyra subflava, Sitotrogacerealella, Sparganothis pilleriana, Spilonota lechriaspis; S. ocellana,Spodoptera (=Lamphygma) spp. such as S. cosmoides, S. eridania, S.exigua, S. frugiperda, S. latisfascia, S. littoralis, S. litura, S.omithogalli; Stigmella spp., Stomopteryx subsecivella, Strymon bazochii,Sylepta derogata, Synanthedon spp. such as S. exitiosa, Teciasolanivora, Telehin licus, Thaumatopoea pityocampa, Thaumatotibia(=Cryptophlebia) leucotreta, Thaumetopoea pityocampa, Thecla spp.,Theresimima ampelophaga, Thyrinteina spp, Tildenia inconspicuella, Tineaspp. such as T. cloacella, T. pellionella; Tineola bisselliella, TortriXspp. such as T. vindana; Trichophaga tapetzella, Trichoplusia spp. suchas T. ni; Tuta (=Scrobipalpula) absoluta, Udea spp. such as U.rubigalis; U. rubigalis; Virachola spp., Yponomeuta padella, andZeiraphera canadensis

insects from the order of Coleoptera, for example Acalymma vittatum,Acanthoscehdes obtectus, Adoretus spp., Agelastica Agrilus spp. such asA. anxius, A. planipennis; A. sinuatus; Agriotes spp. such as A.fuscicollis; A. lineatus, A. obscurus; Alphitoblus diaperinus,Amphimallus Anisandrus dispar, Anisoplia austriaca, Anoblum punctatum,Anomala corpulenta, Anomala rufocuprea, Anoplophora spp. such as A.glabripennis Anthonomus spp. such as A. eugenii; A. grandis, A. pomorum;Anthrenus spp., Aphthona euphoridae, Apion spp., Apogonia spp., Athoushaemorrhoidalis; Atomaria spp. such as A. linearis; Attagenus spp.,Aulacophora femoralis, Blastophagus piniperda, Blitophaga undata,Bruchidius obtectus, Bruchus spp. such as B. lentis; B. pisorum, B.rufimanus; Byctiscus betulae, Callidiellum rufipenne, Callopistriaflondensis; Callosobruchus chinensis; Cameraria ohndella, Cassidanebulosa, Cerotoma trifurcata, Cetonia aurata, Ceuthorhynchus spp. suchas C. assimilis; C. napi; Chaetocnema tibialis, Cleonus mendicus,Conoderus spp. such as C. vespertinus; Conotrachelus nenuphar,Cosmopolites spp., Costelytra zealandica, Crioceris asparagl,Cryptolestes ferrugineus, Cryptorhynchus lapathi Ctenicera spp. such asC. destructor; Curcullo spp., Cylindrocopturus spp., Cyclocephala spp.,Dactylispa balyi, Dectes texanus, Dermestes spp., Diabrotica spp. suchas D. undecimpunctata, D. speciosa, D. longicornis; D. semipunctata, D.virgifera; Diaprepes abbreviates, Dichocrocis spp., Dicladispa armigera,Diloboderus abderus, Diocalandra frumenti (Diocalandra stigmaticollis),Enaphalodes rufulus, Epilachna spp. such as E. varivestis; E.vigintioctomaculata; Epitrix spp. such as E. hirtipennis; E. similaris;Eutheola humilis, Eutinobothrus brasillensis; Faustinus cubae, Gibbiumpsylloides, Gnathocerus cornutus, Hellula undalis; Heteronychus arator,Hylamorpha elegans, Hylobius abietis; Hylotrupes bajulus, Hypera spp.such as H. brunnelpennis; H. postica; Hypomeces squamosus, Hypothenemusspp., Ips typographus, Lachnostema consanguinea, Lasioderma serricome,Latheticus oryzae, Lathridius spp., Lema spp. such as L. bilineata, L.melanopus; Leptinotarsa spp. such as L. decemlineata; Leptispa pygmaea,Limonius californicus, Lissorhoptrus oryzophilus, Lixus spp., Luperodesspp., Lyctus spp such as L. bruneus; Liogerys fuscus, Macrodactylus spp.such as M. subspinosus; Maladera matrida, Megaplatypus mutates,Megascelis spp., Melanotus communis, Meligethes spp. such as M. aeneus;Melolontha spp. such as M. hippocastani, M. melolontba; Metamasiushemipterus, Microtheca spp., Migdolus spp. such as M. fryanus,Monochamus spp. such as M. alternatus; Naupactus xanthographus, Niptushololeucus, Oberia brevis, Oemona hirta, Oryctes rhinoceros,Oryzaephifus surinamensis, Oryzaphagus oryzae, Otiorrhynchus sulcatus,Otiorrhynchus ovatus, Otiorrhynchus sulcatus, Oulema melanopus, Oulemaoryzae, Oxycetonia jucunda, Phaedon spp. such as P. brassicae, P.cochieariae; Phoracantha recurva, Phyllobius pyri, Phylloperthahorticola, Phyllophaga spp. such as P. helleri; Phyilotreta spp. such asP. chrysocephaia, P. nemorum, P. striolata, P. vittula; Phylloperthahorticola, Popillia japonica, Premnotrypes spp., Psacothea hifaris,Psylliodes chrysocephaia, Prostephanus truncates, Psylliodes spp.,Ptinus spp., Pulga saltona, Rhizopertha dominica, Rhynchophorus spp.such as R. billineatus, R. ferrugineus, R. palmarum, R. phoenicis, R.vulneratus; Saperda Candida, Scolytus schevyrewi, Scyphophorusacupunctatus, Sitona lineatus, Sitophilus spp. such as S. granaria, S.oryzae, S. zeamais; Sphenophorus spp. such as S. levis; Stegobiumpaniceum, Sternechus spp. such as S. subsignatus; Strophomorphusctenotus, Symphytetes spp., Tanymecus spp., Tenebrio molitor,Tenebrioides mauretanicus, Tribolium spp. such as T. castaneum;Trogoderma spp., Tychius spp., Xylotrechus spp. such as X. pyrrhoderus;and, Zabrus spp. such as Z. tenebrioides;

insects from the order of Diptera for example Aedes spp. such as A.aegypti, A. albopictus, A. vexans; Anastrepha ludens, Anopheles spp.such as A. albimanus, A. crucians, A. freeborni, A. gambiae, A.leucosphyrus, A. maculipennis, A. minimus, A. quadrimaculatus, A.sinensis; Bactrocera invadens, Bibio hortufanus, Calliphoraerythrocephala, Calliphora vicina, Ceratitis capitata, Chrysomyia spp.such as C. bezziana, C. hominivorax, C. macellaria; Chrysops atlanticus,Chrysops discalis, Chrysops silacea, Cochliomyia spp. such as C.hominivorax; Contarinia spp. such as C. sorghicola; Cordytobiaanthropophaga, Culex spp. such as C. nigripalpus, C. pipiens, C.quinquefasciatus, C. tarsalis, C. tritaeniorhynchus; Culicoides furens,Culiseta inornata, Culiseta melanura, Cuterebra spp., Dacus cucurbitae,Dacus oleae, Dasineura brassicae, Dasineura oxycoccana, Delia spp. suchas D. antique, D. coarctata, D. platura. D. radicum; Dermatobia hominis,Drosophila spp. such as D. suzukii, Fannia spp. such as F. canicularis;Gastraphilus spp. such as G. intestinalis; Geomyza tipunctata, Glossinaspp. such as G. fuscipes, G. morsitans, G. palpalis, G. tachinoides;Haematobia irritans, Haplodiplosis equestris, Hippelates spp., Hylemyiaspp. such as H. platura; Hypoderma spp. such as H. lineata; Hyppoboscaspp., Hydrellia philippina, Leptoconops torrens, Liriomyza spp. such asL. sativae, L. trifolii; Lucifa spp. such as L. caprina, L. cuprina, Lsericata; Lycoria pectoralis, Mansonia titillanus, Mayetiola spp. suchas M. destructor; Musca spp. such as M. autumnalis, M. domestica;Muscina stabulars, Oestrus spp. such as O. ovis; Opomyza florum,Oscinella spp. such as O. frit; Orseolia oryzae, Pegomya hysocyami,Phlebotomus argentipes, Phorbia spp. such as P. antiqua, P. brassicae,P. coarctata; Phytomyza gymnostoma, Prosimulium mixtum, Psila rosae,Psorophora columbiae, Psorophora discolor, Rhagofetis spp. such as R.cerasi, R. cingutate, R. indifferens, R. mendax, R. pomonella; Rivelliaquadrifasciata, Sarcophaga spp. such as S. haemorrhoidalis; Simuliumvittatum, Sitodipfosis mosellana, Stomoxys spp. such as S. calcitrans;Tabanus spp. such as T. atratus, T. bovinus, T. lineola, T. similis;Tannia spp, Thecodiplosis japonensis, Tipula oleracea, Tipula paludosa,and Wohlfahrtia spp;

-   -   insects from the order of Thysanoptera for example, Baliothrips        biformis, Dichromothrips corbetti, Dichromothrips ssp.,        Echinothrips americanus, Enneothrips flavens, Frankliniella spp.        such as F. fusca, F occidentalis, F. tritici; Heliothnps spp,        Hercinothrips femoralis, Kakothrips spp., Microcephalothrips        abdominalis, Neohydatothrips samayunkur, Pezothrips kellyanus,        Rhipiphorothrips cruentatus, Scirtothrips spp. such as S.        citri, S. dorsalis, S. perseae; Stenchaetothrips spp,        Taeniothrips cardamoni, Taeniothrips inconsequens, Thrips spp.        such as T. imagines, T. hawaiiensis, T. oryzae, T. palmi, T.        parvispinus, T. tabaci;    -   insects from the order of Hemiptera for example, Acizzia        jamatonica, Acrosternum spp. such as A. hilare; Acyrthosipon        spp. such as A. onobrychis, A. pisum; Adelges laricis, Adelges        tsugae, Adelphocoris spp., such as A. rapidus, A. superbus;        Aeneolamia spp., Agonoscena spp., Aulacorthum solani,        Aleurocanthus woglumi, Aleurodes spp., Aleurodicus disperses,        Aleurolobus barodensis, Aleurothrixus spp., Amrasca spp., Anasa        tristis, Antestiopsis spp., Anuraphis cardui, Aonidiella spp.,        Aphanostigma piri, Aphidula nasturtrii, Aphis spp. such as A.        craccivora, A. fabae, A. forbesi, A. gossypii, A.        grossutariae, A. maiditadicis, A. pomi, A. sambuci, A.        schneideri, A. spiraecofa; Arboridia apicalis, Arilus critatus,        Aspioiella spp., Aspidiotus spp., Atanus spp., Aulacaspis        yasumatsui, Aulacorthum solani, Bactericera cockerelli        (Paratrioza cockerelli), Bemisia spp. such as B.        argentifolii, B. tabaci (Aleurodes tabaci); Blissus spp. such        as B. leucopterus; Brachycaudus spp. such as B. cardui, B.        helichrysi, B. persicae, B. prunicola; Brachycolus spp.,        Brachycorynella asparagi, Brevicoryne brassicae, Cacopsylla spp.        such as C. fulguralis, C. pyricola (Psylla piri); Calligypona        marginata, Calocoris spp., Campylomma livida, Capitophorus        horni, Carneocephala fulgida, Cavelerius spp., Ceraplastes spp.,        Ceratovacuna lanigera, Ceroplastes ceriferus, Cerosipha        gossypii, Chaetosiphon fragaefolii, Chionaspis tegalensis,        Chlorita onukii, Chromaphis juglandicola, Chrysomphalus ficus,        Cicadulina mbila, Cimex spp. such as C. hemipterus, C.        lectularius; Coccomytilus halli, Coccus spp. such as C.        hesperidum, C. pseudomagnoliarurum, Corythucha arcuata,        Creontiades dilutus, Cryptomyzus ribis, Chrysomphalus aonidum,        Cryptomyzus ribis, Ctenarytaina spatulata, Cyrtopeltis notatus,        Dalbulus spp., Dasynus piperis, Dialeurodes spp. such as D.        citrifolii; Dalbulus maidis, Diaphorina spp. such as D. citri;        Diaspis spp. such as D. bromeliae; Dichelops furcatus,        Diconocoris hewetti, Doratis spp., Dreyfusia nordmannianae,        Dreyfusia piceae, Drosicha spp., Dysaphis spp. such as D.        plantaginea, D. pyri, D. radicola; Dysaulacorthum pseudosolani,        Dysdercus spp. such as D. cingulatus, D. intermedius;        Dysmicoccus spp., Edessa spp., Geocoris spp., Empoasca spp. such        as E. fabae, E. sofana; Epidiaspis leperii, Eriosoma spp. such        as E. lanigerum, E. pyricola; Erythroneura spp., Eurygaster spp.        such as E. integriceps; Euscelis biiobatus, Euschistus spp. such        as E. heros, E. impictiventris, E. servus; Fiorinia theae,        Geococcus coffeae, Glycaspis brimblecombei, Hatyomorpha spp.        such as H. halys; Heliopeltis spp., Homalodisca vitripennis (=H.        coagulata) Horcias nobifellus, Hyalopterus pruni, Hyperomyzus        actucae, Icerya spp. such as I. purchase; Idiocerus spp.,        Idioscopus spp., Laodelphax striatellus, Lecanium spp.,        Lecanoideus floccissimus, Lepioosaphes spp. such as L. ulmi;        Leptocorisa spp., Leptogfossus phyllopus, Lipaphis erysimi,        Lygus spp. such as L. hesperus, L. lineolaris, L. pratensis;        Maconellicoccus hirsutus, Marchalina hellenica, Macropes        excavatus, Macrosiphum spp. such as M. rosae, M. avenae, M.        euphorbiae; Macrosteles quadrilineatus, Mahanarva fimbriolata,        Megacopta cribraria, Megoura viciae, Melanaphis pyarius,        Melanaphis sacchari, Melanocallis (=Tinocallis) caryaefoliae,        Metcafiella spp., Metopolopbium dirhodum, Monellia costatis,        Monelliopsis pecanis, Myzocallis coryli, Murgantia spp., Myzus        spp. such as M. ascalonicus, M. cerasi, M. nicotianae, M.        persicae, M. varians; Nasonovia ribis-nigri, Neotoxoptera        formosana, Neomegalotomus spp, Nephotettix spp. such as N.        malayanus, N. nigropictus, N. parvus, N. virescens; Nezara spp.        such as N. viridula; Nilaparvata lugens, Nysius huttoni, Oebalus        spp. such as O. pugnax; Oncometopia spp., Orthezia praefonga,        Oxycaraenus hyalinipennis, Parabemisia myricae, Pariatoria spp.,        Parthenolecanium spp. such as P. corni, P. persicae; Pemphigus        spp. such as P. bursarius, P. populivenae; Peregrinus maidis,        Perkinsiella saccharicida, Phenacoccus spp. such as P.        aceris, P. gossypii; Phloeomyzus passerinii, Phorodon humuli.        Phylloxera spp. such as P. devastatrix, Piesma quadrata,        Piezodorus spp. such as P. guildinii; Pinnaspis aspidistrae,        Planococcus spp. such as P. citri, P. ficus; Prosapia bicincta,        Protopulvinaria pyriformis, Psallus seriatus, Pseudacysta        persea, Pseudaulacaspis pentagona, Pseudococcus spp. such as P.        comstocki; Psylla spp. such as P. mali; Pteromalus spp.,        Putvinaria amygdali, Pyrilla spp., Quadraspidiotus spp., such        as Q. pemiciosus; Quesada gigas, Rastrococcus spp., Reduvius        senilis, Rhizoecus americanus, Rhodnius spp., Rhopalomyzus        ascaionicus, Rhopalosiphum spp. such as R. pseudobrassicas, R.        insertum, R. maidis, R padi; Sagatodes spp., Sahibergella        singuiaris, Saissetia spp., Sappaphis mala, Sappaphis mali,        Scaptocoris spp., Scaphoides titanus, Schizaphis graminum.        Schizoneura lanuginosa. Scotinophora spp., Selenaspidus        articulatus Sitobion avenae, Sogata spp., Sogatella furcifera.        Sofubea insularis, Spissistitus festinus (=Stictocephaa        festina), Stephanitis nashi, Stephanitis pyrioides, Stephanitis        takeyai, Tenalaphara malayensis, Tetraleurodes perseae,        Therioaphis maculate, Thyania spp. such as T. accerra, T.        perditor; Tibraca spp., Tomaspis spp., Toxoptera spp. such as T.        aurantii; Triafeurodes spp. such as T. abutilonea, T. ridni, T.        vaporariorum; Triatoma spp., Trioza spp., Typhlocyba spp,        Unaspis spp. such as U. citri, U. yanonensis; and Viteus        vitifolii,

Insects from the order Hymenoptera for example Acanthomyops interjectus,Athalia rosae, Alta spp. such as A. capiguara, A. cephalotes, A.cephaiotes, A. laevigata, A. robusta, A. sexdens, A. texana, Bombusspp., Brachymyrmex spp., Camponotus spp. such as C. fioridanus, C.pennsytvanicus, C. modoc; Cardiocondyla nuda, Chalibion sp,Crematogaster spp., Dasymutilla occidental, Diprion spp., Dolichovespulamaculata, Dorymyrmex spp., Dryocosmus kuriphiius, Formica spp.,Hoplocampa spp. such as H. minuta. H. testudinea; Iridomyrmex humilis,Lasius spp. such as L. niger, Linepithema humile, Liometopum spp.,Leptocybe invasa, Monomorium spp. such as M. pharaonis, Monomorium,Nytandria futva, Pachycondyla chinensis, Paratrechina tongicomis, Paravespula spp., such as P. germanica. P. pennsyivanica, P. vulgaris;Pheidole spp. such as P. megacephala; Pogonomyrmex spp. such as P.barbatus. P. californicus, Polistes rubiginosa. Prenolepis impairs,Pseudomyrmex gracilis, Schelipron spp., Sirex cyaneus, Sofenopsis spp.such as S. geminata, S. invicta, S. molesta, S. richteri, S. xyloni,Sphecius speciosus, Sphex spp., Tapinoma spp. such as T. melanocephalum,T. sessile; Telramorium spp. such as T. caespitum, T. bicarinatum. Vespaspp. such as V. crabro; Vespula spp. such as V. squamosal; Wasmanniaauropunctata, Xylocopa sp;

Insects from the order Orthoptera for example Acheta domesticus,Calliptamus italicus, Chortoicetes terminifera, Ceuthophllus spp.,Diastrammena asynamora, Dociostaurus maroccanus, Gryllotalpa spp. suchas G. africana, G. gryllotalpa; Gryllus spp., Hieroglyphus daganensis;Kraussaria angulifera, Locusta spp. such as L. migratoria, L. pardallna;Melanoplus spp. such as M. bivittatus, M. femurrubrum, M. mexicanus, M.sanguinipes, M. spretus; Nomadacris septemfasciata, Oedaleussenegalensls; Scapteriscus spp., Schistocerca spp. such as S. americana,S. gregaria, Stemopelmatus spp., Tachycines asynamorus, and Zonozerusvarlegatus

Pests from the Class Arachnida for example Acari, e.g. of the familiesArgasidae, Ixodidae and Sarcoptidae, such as Amblyomma spp. (e.g. A.americanum, A. variegatum, A. maculatum), Argas spp. such as A.persicu), Boophilus spp. such as B. annulatus, B. decoloratus, B.microplus, Dermacentor spp. such as D. silvarum, D. andersoni, D.variabills; Hyalomma spp. such as H. truncatum, Ixodes spp. such as I.ricinus, I. rubicundus, I. scapularis, I. holocyclus, I. pacificus,Rhipicephalus sanguineus, Ornithodorus spp. such as O. moubata, O.hermsi, O. turicata, Ornithonyssus bacoti, Otobius megnini, Dermanyssusgallinae, Psoroptes spp. such as P. ovis, Rhipicephalus spp. such as R.sanguineus, R. appendiculatus, Rhipicephalus evertsi, Rhizoglyphus spp.,Sarcoptes spp. such as S. Scablei, and Family Eriophyidae includingAceria spp. such as A. sheldone; A. anthocoptes, Acallitus spp., Aculopsspp. such as A. lycopersici, A. pelekassi, Aculus spp. such as A.schlechtendali; Colomerus vitis, Epitrimerus pyri, Phyllocoptrutaoleivora; Eriophytes ribis and Eriophyes spp. such as Eriophyessheldoni, Family Tarsonemidae including Hemitarsonemus spp., Phytonemuspallidus and Polyphagotarsonemus latus, Stenotarsonemus spp.Steneotarsonemus spinki, Family Tenuipalpidae including Brevipalpus spp.such as B. phoenicis; Family Tetranychidae including Eotetranychus spp.,Eutetranychus spp., Oligonychus spp., Petrobia latens, Tetranychus spp.such as T. cinnabarinus, T. evansi, T. kanzawai, T. pacificus, T.phaseulus, T. telarius and T. urticae, Bryobia praetiosa, Panonychusspp. such as P. ulmi, P. citri, Metatetranychus spp. and Oligonychusspp. such as O. pratensis, O. perseae, Vasates lycopersici, Raoiellaindica, Family Carpoglyphidae including Carpoglyphus spp.; Penthaleidaespp. such as Halotydeus destructor, Family Demodicidae with species suchas Demodex spp; Family Trombkidea including Trombicula spp.; FamilyMacronyssidae including Ornothonyssus spp.; Family Pyemotidae includingPyemotes tritici, Tyrophagus putrescentiae, Family Acaridae includingAcarus siro, Family Araneida including Lalrodectus mactans, Tegenariaagrestis, Chiracanthium sp, Lycosa sp Achaearanea tepidariorum andLoxosceles redusa,

Pests from the Phylum Nematoda, for example, plant parasitic nematodessuch as root-knot nematodes, Meloidogyne spp. such as M. hapta, M.incognita, M. javanica; cyst-forming nematodes, Globodera spp. such asG. rostocbiensis; Heterodera spp. such as H. avenae, H. glycines, H.schachtii, H. trifolii; Seed gall nematodes, Anguina spp.; Stem andfoliar nematodes, Apheienchoides spp. such as A. besseyi; Stingnematodes, Belonolaimus spp. such as B. fongicaudatus; Pine nematodes,Bursapheienchus spp. such as B. lignicolus, B. xylophilus; Ringnematodes, Criconema spp., Criconemella spp. such as C. xenoplax and C.ornata; and, Criconemoides spp. such as Criconemoides informis;Mesocriconema spp.; Stem and bulb nematodes, Dityienchus spp. such as D.destructor, D. dipsaci; Awl nematodes, Dolichodorus spp.; Spiralnematodes, Heliocotylenchus multicinctus; Sheath and sheathoidnematodes, Hemicycliophora spp. and Hemicriconemoides spp.;Hirshmanniella spp.; Lance nematodes, Hoploaimus spp.; False rootknotnematodes, Nacobbus spp.; Needle nematodes, Longidorus spp. such as L.elongalus; Lesion nematodes, Pratylencbus spp. such as P. brachyurus, P.neglectus, P. penetrans, P. curvitatus, P. goodeyi; Burrowing nematodes,Radopbolus spp. such as R. similis; Rhadopbolus spp.; Rbodopholus spp.;Reniform nematodes, Rotylenchus spp. such as R. robustus, R. reniformis;Scutellonema spp.; Stubby-root nematode, Trichodorus spp. such as T.obtusus, T. primitivus; Paratrichodorus spp. such as P. minor; Stuntnematodes, Tyienchorhynchus spp. such as T. daytoni, T. dubius; Citrusnematodes, Tyienchulus spp. such as T. semipenetrans; Dagger nematodes,Xiphinema spp.; and other plant parasitic nematode species;

Insects from the order Isoptera for example Calotermes flavicoilis,Coptotermes spp. such as C. formosanus, C. geslroi, C. acinaciformis;Cornitermes cumulans, Cryptotermes spp. such as C. brevis, C. cavifrons;Globilermes sutfureus, Heterotermes spp. such as H. aureus, H.longiceps, H. tenuis; Leucotermes flavipes, Odontotermes spp.,incisitermes spp. such as I. minor, I. Snyder, Marginitermes hubbardi,Mastotermes spp. such as M. darwiniensis Neocapritermes spp. such as N.opacus N. parvus; Neotermes spp., Procornitermes spp., Zootermopsis spp.such as Z. angusticollis, Z. nevadensis, Reticulitermes spp. such as R.hesperus, R. tibialis R. speratus, R. fiavipes, R. grassei, R.lucifugus, R. santonensis, R. virginicus; Termes nataiensis,

Insects from the order Blattaria for example Blatta spp. such as B.orientalis, B. lateralis; Blattella spp. such as B. asahinae, B.germanica; Leucophaea maderae, Panchlora nivea, Peripfaneta spp. such asP. americana, P. austraiasiae, P. brunnea, P. fuligginosa, P. japonica;Supella longipalpa, Parcoblatta pennsylvanica, Eurycotis fioridana,Pycnoscelus surinamensis,

Insects from the order Siphonoptera for example Cediopsylla simples,Ceratophyllus spp., Ctenocephalides spp. such as C. felis, C. canis,Xenopsylla cheopis, Putex irritans, Trichodectes canis, Tunga penetransand Nosopsyllus fasciatus,

Insects from the order Thysanura for example Lepisma saccharina,Ctenolepisma urbana, and Thermobia domestica.

Pests from the class Chilopoda for example Geophilus spp., Scutigeraspp. such as Scutigera coleoptrata,

Pests from the class Diplopoda for example Blaniulus guttulatus, Julusspp., Narceus spp.,

Pests from the class Symphyla for example Scutigerella immaculata,

Insects from the order Dermaptera, for example Forficula auricularia,

Insects from the order Collembola, for example Onychiurus spp., such asOnychiurus armatus,

Pests from the order Isopoda for example, Armadillidium vufgare, Oniscusasellus, Porcellio scaber,

Insects from the order Phthiraptera, for example Damalinia spp.,Pediculus spp. such as Pediculus humanus capitis. Pediculus humanuscorporis, Pediculus humanus humanus; Pthirus pubis, Haematopinus spp.such as Haematopinus eurysternus, Haematopinus suis, Linognathus spp.such as Linognathus vituli; Bovicofa bovis, Menopon gallinae,Menacanthus stramineus and Solenopotes capillatus, Trichodectes spp.,

Examples of further pest species which may be controlled by compounds offormula (I) include: from the Phylum Mollusca, class Bivalvia, forexample, Dreissena spp.; class Gastropoda, for example, Arion spp.,Biomphalaria spp., Bulinus spp., Deroceras spp., Galba spp., Lymnaeaspp., Oncomelania spp., Pomacea canaliclata, Succinea spp; from theclass of the helminths, for example, Ancylostoma duodenale, Ancylostomaceylanicum, Acylostoma braziliensis, Ancylostoma spp., Ascarislumbricoides, Ascaris spp., Brugia matayi, Brugia timori, Bunostomumspp., Chabertia spp., Cbnorchis spp., Coopeha spp., Dicrocoellum spp.,Dictyocaulus filaria, Diphyllobothrium latum, Dracuncutus medinensis,Echinococcus granulosus, Echinococcus multilocularis, Enterobiusvermicularis, Faciola spp., Haemonchus spp. such as Haemonchuscontortus; Heterakis spp., Hymertolepis nana, Hyostrongufus spp., LoaLoa, Nematodirus spp., Oesophagostomum spp., Opisthorchis spp.,Onchocerca volvulus. Ostertagia spp., Paragonimus spp., Schistosomenspp., Strongybides fuellebomi, Strongyloides stercora lis, Stronybidesspp., Taenia saginata. Taenia solium, Trichinella spiralis, Trichinellanativa, Trichinella britovi, Trichinella nelsoni, Trichinellapseudopsirafis, Trichostrongufus spp, Trichuris trichiura, Wuchereriabancrofti.

Animal Health

The compounds of the present invention are suitable for use in treatingor protecting animals against infestation or infection by parasites.Therefore, the present invention also relates to the use of a compoundof the present invention for the manufacture of a medicament for thetreatment or protection of animals against infestation or infection byparasites. Furthermore, the present invention relates to a method oftreating or protecting animals against infestation and infection byparasites, which comprises orally, topically or parenterallyadministering or applying to the animals a parasiticidally effectiveamount of a compound of the present invention. The present inventionalso relates to the non-therapeutic use of compounds of the presentinvention for treating or protecting animals against infestation andinfection by parasites. Moreover, the present invention relates to anon-therapeutic method of treating or protecting animals againstinfestation and infection by parasites, which comprises applying to alocus a parasiticidally effective amount of a compound of the presentinvention.

The compounds of the present invention are further suitable for use incombating or controlling parasites in and on animals. Furthermore, thepresent invention relates to a method of combating or controllingparasites in and on animals, which comprises contacting the parasiteswith a parasitically effective amount of a compound of the presentinvention.

The present invention also relates to the non-therapeutic use ofcompounds of the present invention for controlling or combatingparasites. Moreover, the present invention relates to a non-therapeuticmethod of combating or controlling parasites, which comprises applyingto a locus a parasiticidally effective amount of a compound of thepresent invention.

The compounds of the present invention can be effective through bothcontact (via soil, glass, wall, bed net, carpet, blankets or animalparts) and ingestion (e.g. baits). Furthermore, the compounds of thepresent invention can be applied to any and all developmental stages.

The compounds of the present invention can be applied as such or in formof compositions comprising the compounds of the present invention.

The compounds of the present invention can also be applied together witha mixing partner, which acts against pathogenic parasites, e.g. withsynthetic coccidiosis compounds, polyetherantibiotics such as Amprolium,Robenidin, Toltrazuril, Monensin, Salinomycin, Maduramicin, Lasalocid,Narasin or Semduramicin, or with other mixing partners as defined above,or in form of compositions comprising said mixtures.

The compounds of the present invention and compositions comprising themcan be applied orally, parenterally or topically, e.g. dermally. Thecompounds of the present invention can be systemically ornon-systemically effective.

The application can be carried out prophylactically, therapeutically ornon-therapeutically. Furthermore, the application can be carried outpreventively to places at which occurrence of the parasites is expected.

As used herein, the term “contacting” includes both direct contact(applying the compounds/compositions directly on the parasite, includingthe application directly on the animal or excluding the applicationdirectly on the animal, e.g. at it's locus for the latter) and indirectcontact (applying the compounds/compositions to the locus of theparasite). The contact of the parasite through application to its locusis an example of a non-therapeutic use of the compounds of the presentinvention.

The term “locus” means the habitat, food supply, breeding ground, area,material or environment in which a parasite is growing or may growoutside of the animal.

As used herein, the term “parasites” includes endo- and ectoparasites.In some embodiments of the present invention, endoparasites can bepreferred. In other embodiments, ectoparasites can be preferred.Infestations in warm-blooded animals and fish include, but are notlimited to, lice, biting lice, ticks, nasal bots, keds, biting flies,muscoid flies, flies, myiasitic fly larvae, chiggers, gnats, mosquitoesand fleas.

The compounds of the present invention are especially useful forcombating parasites of the following orders and species, respectively:

fleas (Siphonaptera), e.g. Ctenocephalides felis, Ctenocephalides canis;Xenopsylla cheopis, Pulex irritans, Tunga penetrans, and Nosopsyllusfasciatus; cockroaches (Blattaria-Blattodea), e.g. Blattella germanica,Blattella asahinae, Periplaneta americana, Periplaneta japonica,Periplaneta brunnea, Periplaneta fuligginosa, Periplaneta australasiae,and Blatta orientalis; flies, mosquitoes (Diptera), e.g. Aedes aegyptiAedes albopictus, Aedes vexans, Anastrepha ludens, Anophelesmaculipennis; Anopheles cruclans, Anopheles albimanus, Anophelesgambiae, Anopheles freeborni; Anophelesleucosphyrus, Anopheles minithus,Anopheles quadrimaculatus, Calliphora vicina, Chrysomya bezziana,Chrysomya hominivorax, Chrysomya macellaria, Chrysops discalis; Chrysopssllacea, Chrysops atlanticus, Cochliomyia hominivorax, Cordylobiaanthropophaga, Culicoides furens, Culex piplens, Culex nigripalpus,Culex quinquefasciatus, Culex tarsalis, Culiseta inomata, Culisetamelanura, Dermatobia hominis; Fannia canicularis; Gasterophilusintestinalis, Glossina morsitans, Glossina palpalis, Glossina fuscipes,Glossina tachinoides, Haematobia irritans, Haplocliplosis equestris;Hippelates spp., Hypoderma lineata, Leptoconops torrens, Luciliacaprina, Lucilia cuprina, Lucilia sericata, Lycoria pectoralis, Mansoniaspp., Musca domestica, Muscina stabulans, Oestrus ovis, Phlebotomusargentipes, Psorophora columbiae, Psorophora discolor, Prosimullummixtum, Sarcophaga haemorrhoidalis; Sarcophaga sp., Simulium vittatum,Stomoxys calcitrans, Tabanus bovinus, Tabanus atratus, Tabanus lineola,and Tabanus similis; lice (Phthiraptera), e.g. Pediculus humanuscapitis; Pediculus humanus corporis, Pthirus pubis, Haematopinuseurystemus, Haematopinus suis, Linognathus vituli, Bovicola bovis,Menopon galinae, Menacanthus stramineus and Solenopotes capillatus;ticks and parasitic mites (Parasitiformes): ticks (Ixodida), e.g. Ixodesscapularis; Ixodes holocyclus, Ixodes pacificus, Rhiphicephalussanguineus, Dermacentor andersoni Dermacentor variabills; Amblyommaamericanum, Ambryomma maculatum, Ornithodorus hermsi; Ornithodorusturicata and parasitic mites (Mesostigmata), e.g. Ornithonyssus bacotiand Dermanyssus gallinae, Actinedida (Prostigmata) and Acaridida(Astigmata), e.g. Acarapis spp., Cheyletiella spp., Ornithocheyletiaspp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp.,Listrophorus spp., Acarus spp., Tyrophagus spp., Caloglyphus spp.,Hypodectes spp., Pterolichus spp., Psoroptes spp., Chorioptes spp.,Otodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp.,Cytodites spp., and Laminosioptes spp; Bugs (Heteropterida): Cimexlectularius, Cimex hemipterus, Reduvius senilis, Triatoma spp., Rhodniusssp., Panstrongylus ssp., and Arilus critatus; Anoplurida, e.g.Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., andSolenopotes spp.; Mallophagida (suborders Arnblycerina andIschnocerina), e.g. Trimenopon spp., Menopon spp., Trinoton spp.,Bovicola spp., Werneckiella spp., Lepikentron spp., Trichodectes spp.,and Felicola spp.; Roundworms Nematoda: Wipeworms and Trichinosis(Trichosyringida), e.g. Trichinellidae (Trichinella spp.), (Trichuridae)Trichuris spp., Capillaria spp.; Rhabditida, e.g. Rhabditis spp.,Strongyloides spp., Helicephalobus spp.; Strongylida, e.g. Strongylusspp., Ancylostoma spp., Necator americanus, Bunostomum spp. (Hookworm),Trichostrongylus spp., Haemonchus contortus, Ostertagia spp., Cooperiaspp., Nematodirus spp., Dictyocaulus spp., Cyathostoma spp.,Oesophagostomum spp., Stephanurus dentatus, Ollulanus spp., Chabertiaspp., Stephanurus dentatus, Syngamus trachea, Ancylostoma spp.,Uncinaria spp., Globocephalus spp., Necator spp., Metastrongylus spp.,Muellerius capillaris; Protostrongylus spp., Angiostrongylus spp.,Parelaphostrongylus spp., Aleurostrongylus abstrusus, and Dioctophymarenale; Intestinal roundworms (Ascaridida), e.g. Ascaris lumbricoides,Ascaris suum, Ascaridia galli, Parascaris equorum, Enterobiusvermicularis (Threadworm), Toxocara canis, Toxascaris leonine,Skrjabinema spp., and Oxyuris equi; Camallanida, e.g. Dracunculusmedinensis (guinea worm); Spirurida, e.g. Thelazia spp., Wuchereriaspp., Brugia spp., Onchocerca spp., Dirofilari spp. a, Dipetalonemaspp., Setaria spp., Elaeophora spp., Spirocerca lupi, and Habronemaspp.; Thorny headed worms (Acanthocephala), e.g. Acanthocephalus spp.,Macracanthorhynchus hirudinaceus and Oncicola spp.; Planarians(Plathelminthes): Flukes (Trematoda), e.g. Faciola spp., Fascioloidesmagna, Paragonimus spp., Dicrocoelium spp., Fasciolopsis buski;Clonorchis sinensis, Schistosoma spp., Trichobilharzla spp., Alariaalata, Paragonimus spp., and Nanocyetes spp.; Cercomeromorpha, inparticular Cestoda (Tapeworms), e.g. Diphyllobothnum spp., Tenia spp.,Echinococcus spp., Dipylidlum caninum, Multiceps spp., Hymenolepis spp.,Mesocestoides spp., Vamplrolepis spp., Moniezia spp., Anoplocephalaspp., Sirometra spp., Anoplocephala spp., and Hymenolepis spp.

As used herein, the term “animal” includes warm-blooded animals(including humans) and fish. Preferred are mammals, such as cattle,sheep, swine, camels, deer, horses, pigs, poultry, rabbits, goats, dogsand cats, water buffalo, donkeys, fallow deer and reindeer, and also infur-bearing animals such as mink, chinchilla and raccoon, birds such ashens, geese, turkeys and ducks and fish such as fresh- and salt-waterfish such as trout, carp and eels. Particularly preferred are domesticanimals, such as dogs or cats.

In general, “parasiticidally effective amount” means the amount ofactive ingredient needed to achieve an observable effect on growth,including the effects of necrosis, death, retardation, prevention, andremoval, destruction, or otherwise diminishing the occurrence andactivity of the target organism. The parasiticidally effective amountcan vary for the various compounds/compositions used in the invention. Aparasiticidally effective amount of the compositions will also varyaccording to the prevailing conditions such as desired parasiticidaleffect and duration, target species, mode of application, and the like.

Generally, it is favorable to apply the compounds of the presentinvention in total amounts of 0.5 mg/kg to 100 mg/kg per day, preferably1 mg/kg to 50 mg/kg per day.

For oral administration to warm-blooded animals, the formula I compoundsmay be formulated as animal feeds, animal feed premixes, animal feedconcentrates, pills, solutions, pastes, suspensions, drenches, gels,tablets, boluses and capsules. In addition, the formula I compounds maybe administered to the animals in their drinking water. For oraladministration, the dosage form chosen should provide the animal with0.01 mg/kg to 100 mg/kg of animal body weight per day of the formula Icompound, preferably with 0.5 mg/kg to 100 mg/kg of animal body weightper day.

Alternatively, the formula I compounds may be administered to animalsparenterally, for example, by intraruminal, intramuscular, intravenousor subcutaneous injection. The formula I compounds may be dispersed ordissolved in a physiologically acceptable carrier for subcutaneousinjection. Alternatively, the formula I compounds may be formulated intoan implant for subcutaneous administration. In addition the formula Icompound may be transdermally administered to animals. For parenteraladministration, the dosage form chosen should provide the animal with0.01 mg/kg to 100 mg/kg of animal body weight per day of the formula Icompound.

The formula I compounds may also be applied topically to the animals inthe form of dips, dusts, powders, collars, medallions, sprays, shampoos,spot-on and pour-on formulations and in ointments or oil-in-water orwater-in-oil emulsions. For topical application, dips and sprays usuallycontain 0.5 ppm to 5,000 ppm and preferably 1 ppm to 3,000 ppm of theformula I compound. In addition, the formula I compounds may beformulated as ear tags for animals, particularly quadrupeds such ascattle and sheep.

Suitable preparations are:

-   -   Solutions such as oral solutions, concentrates for oral        administration after dilution, solutions for use on the skin or        in body cavities, pouring-on formulations, gels;    -   Emulsions and suspensions for oral or dermal administration;        semi-solid preparations;    -   Formulations in which the active compound is processed in an        ointment base or in an oil-in-water or water-in-oil emulsion        base;    -   Solid preparations such as powders, premixes or concentrates,        granules, pellets, tablets, boluses, capsules; aerosols and        inhalants, and active compound-containing shaped articles.

Compositions suitable for injection are prepared by dissolving theactive ingredient in a suitable solvent and optionally adding furtherauxiliaries such as acids, bases, buffer salts, preservatives, andsolubilizers. Suitable auxiliaries for injection solutions are known inthe art. The solutions are filtered and filled sterile.

Oral solutions are administered directly. Concentrates are administeredorally after prior dilution to the use concentration. Oral solutions andconcentrates are prepared according to the state of the art and asdescribed above for injection solutions, sterile procedures not beingnecessary.

Solutions for use on the skin are trickled on, spread on, rubbed in,sprinkled on or sprayed on. Solutions for use on the skin are preparedaccording to the state of the art and according to what is describedabove for injection solutions, sterile procedures not being necessary.

Gels are applied to or spread on the skin or introduced into bodycavities. Gels are prepared by treating solutions which have beenprepared as described in the case of the injection solutions withsufficient thickener that a clear material having an ointment-likeconsistency results. Suitable thickeners are known in the art.

Pour-on formulations are poured or sprayed onto limited areas of theskin, the active compound penetrating the skin and acting systemically.Pour-on formulations are prepared by dissolving, suspending oremulsifying the active compound in suitable skin-compatible solvents orsolvent mixtures. If appropriate, other auxiliaries such as colorants,bioabsorption-promoting substances, antioxidants, light stabilizers,adhesives are added. Suitable such auxiliaries are known in the art.

Emulsions can be administered orally, dermally or as injections.Emulsions are either of the water-in-oil type or of the oil-in-watertype. They are prepared by dissolving the active compound either in thehydrophobic or in the hydrophilic phase and homogenizing this with thesolvent of the other phase with the aid of suitable emulsifiers and, ifappropriate, other auxiliaries such as colorants, absorption-promotingsubstances, preservatives, antioxidants, light stabilizers,viscosity-enhancing substances. Suitable hydrophobic phases (oils),suitable hydrophilic phases, suitable emulsifiers, and suitable furtherauxiliaries for emulsions are known in the art.

Suspensions can be administered orally or topically/dermally. They areprepared by suspending the active compound in a suspending agent, ifappropriate with addition of other auxiliaries such as wetting agents,colorants, bioabsorption-promoting substances, preservatives,antioxidants, light stabilizers. Suitable suspending agents, andsuitable other auxiliaries for suspensions including wetting agents areknown in the art.

Semi-solid preparations can be administered orally ortopically/dermally. They differ from the suspensions and emulsionsdescribed above only by their higher viscosity.

For the production of solid preparations, the active compound is mixedwith suitable excipients, if appropriate with addition of auxiliaries,and brought into the desired form. Suitable auxiliaries for this purposeare known in the art.

The compositions which can be used in the invention can comprisegenerally from about 0.001 to 95% of the compound of the presentinvention.

Ready-to-use preparations contain the compounds acting againstparasites, preferably ectoparasites, in concentrations of 10 ppm to 80percent by weight, preferably from 0.1 to 65 percent by weight, morepreferably from 1 to 50 percent by weight, most preferably from 5 to 40percent by weight.

Preparations which are diluted before use contain the compounds actingagainst ectoparasites in concentrations of 0.5 to 90 percent by weight,preferably of 1 to 50 percent by weight.

Furthermore, the preparations comprise the compounds of formula Iagainst endoparasites in concentrations of 10 ppm to 2 percent byweight, preferably of 0.05 to 0.9 percent by weight, very particularlypreferably of 0.005 to 0.25 percent by weight.

Topical application may be conducted with compound-containing shapedarticles such as collars, medallions, ear tags, bands for fixing at bodyparts, and adhesive strips and foils.

Generally it is favorable to apply solid formulations which releasecompounds of the present invention in total amounts of 10 mg/kg to 300mg/kg, preferably 20 mg/kg to 200 mg/kg, most preferably 25 mg/kg to 160mg/kg body weight of the treated animal in the course of three weeks.

EXAMPLES

With appropriate modification of the starting materials, the proceduresas described in the preparation examples below were used to obtainfurther compounds of formula I. The compounds obtained in this mannerare listed in the table X that follows, together with physical data.

Compounds can be characterized e.g. by coupled High Performance LiquidChromatography/mass spectrometry (HPLC/MS), or by ¹H-NMR and/or by theirmelting points.

Example-(C-1)3-(cyanomethyl)-8-methyl-7-oxo-6-phenyl-2,3-dihydrothiazolo[3,2-a]pyrimidin-4-ium-5-olate

(C-1)

Step 1: 4-amino-2-(tert-butoxycarbonylamino)-4-oxo-butanoic acid

To Compound of DL-Asparagine monohydrate (15.0 gm, 0.114 mol) in 1,4Dioxane (150 ml) and water (150 ml) was added sodium carbonate (14.44gm, 0.136 mol) and Di-tert butyl-dicarbonate (31.29 ml, 0.136 ma). Thenreaction mass was stirred for 16 hr. at ambient temperature. Progress ofreaction was monitored by TLC. After completion of reaction, reactionmass was concentrate under reduced pressure until 1,4-dioxane wasevaporated. Then pH adjusted to 2 with 37% HCl to give white solid thatwas filtered, washed with water and dried under reduced pressure toafford 25.0 g (94.8% yield) of title compound as a solid.

¹H NMR (DMSO-d₆, 500 MHz) δ=12.5 (s, 1H), 7.31 (s, 1H), 6.88 (t, J=14Hz, 2H), 4.25-4.21 (m, 1H), 2.51-2.40 (m, 2H), 1.38 (s, 1H).

Step 2: ethyl 2-(tert-butoxycarbonylamino)-3-cyano-propanoate

To the product of step-1 (15.0 gm, 0.065 mol) in DCM (150 ml) andEthanol (15 ml) was added EDC.HCl (37.4 gm, 0.194 mol) and4-Dimethylaminopyridine (1.57 gm, 0.013 ml) 0° C. after additionReaction mass was stirred for 16 hr. at ambient temperature. Progress ofreaction was monitored by TLC. After completion of reaction, reactionmass was diluted with water (200 ml) and followed by extracting in ethylacetate (100 ml×3). The combined organic extracts were dried overNa₂SO₄, filtered and concentrated under reduced pressure. The crudeproduct was purified by flash chromatography (eluting in 0-30% ethylacetate in heptane as a mobile phase) to afford 7.0 gm (44.7% yield) oftitle compound as a solid.

¹H NMR (DMSO-d₆, 300 MHz) δ=7.65 (d, J=8.4, 1H), 4.35-4.27 (m, 1H),4.14-4.07 (m, 2H), 2.29-2.80 (m, 2H), 1.36 (s, 10H), 1.18 (t, J=7.2,3H).

Step 3: tert-butyl N-[1-(cyanomethyl)-2-hydroxy-ethyl]carbamate

To the product of step-2 (1.8 gm, 0.007 mol) in dry THF (15 ml) wasadded Lithium borohydride 2M (1.85 ml, 0.004 mol) at 0° C. Then reactionmass was heated at 70° C. for 2 hr. Progress of reaction was monitoredby TLC. After completion of reaction, reaction mass was cooled to roomtemp and acidified with 2M KHSO₄ solution to pH 4. After filtration,Filtrate was extracted in ethyl acetate (30 ml×3). The combined organicextracts were dried over Na₂SO₄, filter and concentrated under reducedpressure. The crude product was purified by flash chromatography(eluting in 0-50% ethyl acetate in heptane as a mobile phase) to afford1.3 gm (87.4% yield) of title compound as a liquid.

¹H NMR (DMSO-d₆, 300 MHz) δ=6.98 (d, J=8.4, 1H), 4.95-4.91 (m, 1H),3.65-3.67 (m, 1H), 3.43-3.24 (m, 2H), 2.75-2.55 (m, 1H), 1.39 (s, 9H).

Step 4: 3-amino-4-hydroxy-butanenitrile

To the product of step-3 (0.500 gm, 0.002 mol) in Methanol (5 ml) wasadded 3M Methanolic HCl (5 ml). Reaction mass was stirred for 16 hr. atambient temperature. Progress of reaction was monitored by TLC. Aftercompletion of reaction, reaction mass was concentrated under reducedpressure. diluted with DCM (10 ml) Then added 3M Methanolic ammonia at0° C. NH₄Cl was formed, Filtered it and filtrate was concentrated underreduced pressure to afford 0.200 gm (80.0% yield) of title compound as aLiquid.

¹H NMR (CDCl₃-d₆, 500 MHz) δ=3.68-3.57 (m, 2H), 3.28-3.23 (m, 1H),2.58-2.45 (m, 2H). Step 5:1-[1-(cyanomethyl)-2-hydroxy-ethyl]-3-methyl-thiourea

To the product of step-4 (0.764 gm, 0.008 mol) in dry THF (10 ml) wasadded Methyl Isothiocyanate (0.837 gm, 0.011 mol) at 0′C. Reaction masswas stirred for 16 hr. at ambient temperature. Progress of reaction wasmonitored by TLC. After completion of reaction, Reaction mass wasconcentrated under reduced pressure to afford crude 1.20 gm (90.8%yield) of title compound as a viscous liquid.

LC/MS (method 1): R_(t): 0.84 min; MS: m/z=174.2 (M⁺¹).

Step 6: 2-[(2Z)-2-methyliminothiazolidin-4-yl]acetonitrile

To the product of step-5 (1.20 gm, 0.007 mol) in dry THF (10 ml) wasadded 1,1′Carbonyldiimidazole (1.68 gm, 0.010 mol) at room temperature.Reaction mass was stirred for 16 hr. at ambient temperature. Progress ofreaction was monitored by TLC. After completion of reaction, reactionmass was concentrate under reduced pressure. The crude product waspurified by flash chromatography (eluting in 0-80% ethyl acetate inheptane as a mobile phase) to afford 0.500 gm (46.5% yield) of titlecompound as a solid.

LC/MS (method 1): R_(t): 0.48 min; MS: m/z=156.2 (M⁺¹).

Step 7:3-(cyanomethyl)-8-methyl-7-oxo-6-phenyl-2,3-dihydrothiazolo[3,2-a]pyrimidin-4-ium-5-olate(C-1)

To the product of step-6 (0.200 gm, 0.001 mol) in Toluene (5 ml) washeated at 105° C. for 15 min. Then added Activated ester (0.517 gm 0.001mol) at same temperature. Then reaction mass was heated at 110° C. for 2hr. Progress of reaction was monitored by TLC. After completion ofreaction, reaction mass was cooled to room temperature, concentratedunder reduced pressure. The crude product was purified by flashchromatography (eluting in 0-100% ethyl acetate in heptane as a mobilephase) to afford 0.080 gm (20.5% yield) of title compound as a solid.

LC/MS (method 1): R_(t): 1.18 min; MS: m/z=300.0 (M⁺¹).

¹H NMR (DMSO-d₆, 500 MHz) δ=7.62 (dd J=1.5, 7 Hz, 2H). 7.45 (dd, J=7.5,7.5 Hz, 2H), 7.09 (dd, J=7.5, 7 Hz, 1H), 4.41-4.39 (m, 1H), 4.10-4.08(m, 1H), 3.62-3.59 (m, 1H), 3.41 (s, 3H), 3.31-3.21 (m, 1H), 3.19-3.15(m, 1H),

Examples of compound of formula I given in table Z were prepared usingthe method analogous to preparation of the above examples or byderivatization of the above examples or intermediates thereof, or usingthe method analogous to the methods mentioned in the general procedure.

TABLE Z Example Structure ¹H NMR C-1

¹H NMR (DMSO-d₆, 500 MHz) δ = 7.62 (dd J = 1.5, 7 Hz, 2H). 7.45 (dd, J =7.5, 7.5Hz, 2H), 7.09 (dd, J = 7.5, 7Hz, 1H), 4.41-4.39 (m, 1H),4.10-4.08 (m, 1H), 3.62-3.59(m, 1H), 3.41 (s, 3H), 3.31-3.21 (m, 1H),3.19- 3.15 (m, 1H), C-2

¹H NMR (DMSO-d₆, 500 MHz) δ = 7.55 (d J = 8Hz, 2H). 6.82 (d, J = 8.5Hz,2H), 7.5, 7.5Hz, 4.39-4.38 (m, 1H), 4.09-4.05 (m, 1H), 3.75 (s, 3H),3.61-3.59 (m, 1H), 3.51-3.15 (m, 5H). C-3

¹H NMR (DMSO-d₆, 500 MHz) δ = 8.12 (s, 1H), 8.05 (d, J = 8 Hz, 1H),7.54-7.41 (m, 2H), 5.43-5.42 (m, 1H), 4.11-4.06 (m, 1H), 3.61-3.63 (m,1H), 3.43- 3.40 (m, 4H), 3.20-3.16 (m, 1H). C-4

¹H NMR (500 MHz, DMSO-d₆) δ 7.55 (d, J = 7.4 Hz, 2H), 7.17 (t, J= 7.6Hz, 2H), 7.11-6.70 (m, 2H), 6.06-5.84 (m, 1H), 5.72 (dd, J = 15.3, 8.2Hz, 1H), 4.05 (ddd, J = 46.3,11.7, 8.8 Hz, 1H), 3.66-3.41 (m, 1H), 3.35(d, J = 7.7 Hz, 3H).

Biological Tests

The biological activity of the compounds of formula (I) of the presentinvention can be evaluated in biological tests as described in thefollowing.

General conditions: If not otherwise specified, the test solutions areprepared as follows:

The active compound is dissolved at the desired concentration in amixture of 1:1 (vol:vol) distilled water: acetone. The test solution isprepared at the day of use.

Test solutions are prepared in general at different concentrations(wt/vol).

Orchid Thrips (Dichromothrips corbetti)

Dichromothrips corbetti adults used for bioassay are obtained from acolony maintained continuously under laboratory conditions. For testingpurposes, the test compound is diluted in a 1:1 mixture of acetone:water(vol:vol), plus 0.01% vol/vol Alkamuls® EL 620 surfactant.

Thrips potency of each compound is evaluated by using a floral-immersiontechnique. Plastic petri dishes are used as test arenas. All petals ofindividual, intact orchid flowers are dipped into treatment solution andallowed to dry. Treated flowers are placed into individual petri dishesalong with about 20 adult thrips. The petri dishes v then covered withlids. All test arenas are held under continuous light and a temperatureof about 28° C. for duration of the assay. After 3 days, the numbers oflive thrips are counted on each flower, and along inner walls of eachpetri dish. The percent mortality is recorded 72 hours after treatment.

In this test, compound C1 at 500 ppm showed over 75% mortality incomparison with untreated controls

Rice Green Leafhopper (Nephotettix virescens)

Rice seedlings are cleaned and washed 24 hours before spraying. Theactive compounds are formulated in 50:50 acetone:water (vol:vol), and0.1% vol/vol surfactant (EL 620) is added. Potted rice seedlings aresprayed with 5 ml test solution, air dried, placed in cages andinoculated with 10 adults. Treated rice plants are kept at about 28-29°C. and relative humidity of about 50-60%. Percent mortality is recordedafter 72 hours.

In this test, compound C1 at 500 ppm showed over 75% mortality incomparison with untreated controls

Rice Brown Plant Hopper (Nilaparvata lugens)

Rice seedlings are cleaned and washed 24 hours before spraying. Theactive compounds are formulated in 50:50 acetone:water (vol:vol) and0.1% vol/vol surfactant (EL 620) is added. Potted rice seedlings aresprayed with 5 ml test solution, air dried, placed in cages andinoculated with 10 adults. Treated rice plants are kept at about 28-29°C. and relative humidity of about 50-60%. Percent mortality is recordedafter 72 hours.

In this test, compound C1 at 500 ppm showed over 75% mortality incomparison with untreated controls

1-15. (canceled)
 16. A substituted pyrimidinium compound of formula (I)

wherein X, Y are each independently O or S; Z is a direct bond, O,S(O)_(m), NR^(b), C(R^(a)R^(aa))O, C(═X¹), C(═X¹)Y¹, or Y¹C(═X¹); X¹ isO, S, or NR^(b); Y¹ is O, S, or NR^(c); A is CH or N and, wherein thenitrogen of the pyrimidinium ring taken together with the contiguouslinking carbon atom and A as depicted in formula (I), form a four- toseven-membered ring, wherein each remaining ring member is selected fromcarbon atoms and up to 3 heteroatoms independently selected from up to 2O, up to 2 S, and up to 3 N(R^(c))_(p), wherein up to 2 carbon atom ringmembers are independently selected from the group consisting of C(═O)and C(═S), and the sulfur atom ring members are independently selectedfrom S(═O)_(m), wherein each ring may be substituted with up to 3 R^(a);R³ is C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₂-C₄-alkenyl, C₂-C₄-haloalkenyl,C₂-C₄-alkynyl, C₂-C₄-haloalkynyl, C₃-C₇-cycloalkyl,C₃-C₇-halocycloalkyl, C₄-C₈-alkylcycloalkyl, C₄-C₈-haloalkylcycloalkyl,C₄-C₈-cycloalkylalkyl, C₄-C₈-halocycloalkylalkyl, C₁-C₆-alkoxy,C₁-C₆-haloalkoxy, C₂-C₆-alkylcarbonyl, C₂-C₆-haloalkylcarbonyl, eachsubstituted with at least one substituent selected from CN, OR^(c),NR^(b)R^(c), NO₂, C(═O)(O)_(p)R^(c), OC(═O)(O)_(p)R^(e),C(═O)NR^(b)R^(c), OC(═O)NR^(b)R^(e), NR^(b)C(═O)(O)_(p)R^(e),NR^(b)C(═O)NR^(b)R^(c), C(═S)NR^(b)R^(c), S(O)_(m)R^(b), SO₂NR^(b)R^(c),OSO₂R^(c), OSO₂NR^(b)R^(c), NR^(b) SO₂R^(c), NR^(b) SO₂NR^(b)R^(c), SF₅,OCN, SCN, Si(R^(d))₃, C(═N(O)_(p)R^(b))R^(b), C(═NNR^(b)R^(c))R^(b),C(═NN(C(═O)O_(p)R^(c))R^(b))R^(b), ON═CR^(b)R^(c), ONR^(b)R^(c),S(═O)_(o)(═NR^(b))_(q)R^(c), SO₂NR^(b)(═O)NR^(b)R^(c), P(═X²)R^(b)R^(c),OP(═X²)(O_(p)R^(c))R^(b), OP(═X²)(OR^(c))₂, N═CR^(b)R^(c),NR^(b)N═CR^(b)R^(c), NR^(b)NR^(b)R^(c), NR^(b)C(═S)NR^(b)R^(c),NR^(b)C(═NR^(b))NR^(b)R^(c), NR^(b)NR^(b)C(═X²)NR^(b)R^(c), NR^(b)NR^(b)SO₂NR^(b)R^(c), or N═S(═O)_(p)R^(c)R^(c), or two geminally bound groupsR³ together may form a group selected from the group consisting of ═O,═S, ═CR^(b)R^(c), ═NR^(c), ═NOR^(c), and ═NNR^(c)R^(c); or R³ is phenyloptionally substituted with one or more substituents selected fromhalogen, CN, OR^(c), NR^(b)R^(c), NO₂, C(═O)(O)_(p)R^(c),OC(═O)(O)_(p)R^(e), C(═O)NR^(b)R^(c), OC(═O)NR^(b)R^(e),NR^(b)C(═O)(O)_(p)R^(e), NR^(b)C(═O)NR^(b)R^(c), C(═S)NR^(b)R^(c),S(O)_(m)R^(b), SO₂NR^(b)R^(c), OSO₂R^(c), OSO₂NR^(b)R^(c), NR^(b)SO₂R^(c), NR^(b) SO₂NR^(b)R^(c), SF₅, OCN, SCN, Si(R^(d))₃,C(═N(O)_(p)R^(b))R^(b), C(═NNR^(b)R^(c))R^(b),C(═NN(C(═O)O_(p)R^(c))R^(b))R^(b), ON═CR^(b)R^(c), ONR^(b)R^(c),S(═O)_(o)(═NR^(b))_(q)R^(c), SO₂NR^(b)(═O)NR^(b)R^(c), P(═X²)R^(b)R^(c),OP(═X²)(O_(p)R^(c))R^(b), OP(═X²)(OR^(c))₂, N═CR^(b)R^(c),NR^(b)N═CR^(b)R^(c), NR^(b)NR^(b)R^(c), NR^(b)C(═S)NR^(b)R^(c),NR^(b)C(═NR^(b))NR^(b)R^(c), NR^(b)NR^(b)C(═X²)NR^(b)R^(c), NR^(b)NR^(b)SO₂NR^(b)R^(c), or N═S(═O)_(p)R^(c)R^(c), or R³ is phenyl optionallysubstituted with one or more substituents selected from C₁-C₄-alkyl,C₁-C₄-haloalkyl, C₂-C₄-alkenyl, C₂-C₄-haloalkenyl, C₂-C₄-alkynyl,C₂-C₄-haloalkynyl, C₃-C₇-cycloalkyl, C₃-C₇-halocycloalkyl,C₄-C₈-alkylcycloalkyl, C₄-C₈-haloalkylcycloalkyl, C₄-C₈-cycloalkylalkyl,C₄-C₈-halocycloalkylalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,C₂-C₆-alkylcarbonyl, C₂-C₆-haloalkylcarbonyl, which groups mayoptionally be substituted with halogen, CN, OR^(c), NR^(b)R^(c), NO₂,C(═O)(O)_(p)R^(c), OC(═O)(O)_(p)R^(e), C(═O)NR^(b)R^(c),OC(═O)NR^(b)R^(e), NR^(b)C(═O)(O)_(p)R^(e), NR^(b)C(═O)NR^(b)R^(c),C(═S)NR^(b)R^(c), S(O)_(m)R^(b), SO₂NR^(b)R^(c), OSO₂R^(c),OSO₂NR^(b)R^(c), NR^(b) SO₂R^(c), NR^(b) SO₂NR^(b)R^(c), SF 5, OCN, SCN,Si(R^(d))₃, C(═N(O)_(p)R^(b))R^(b), C(═NNR^(b)R^(c))R^(b),C(═NN(C(═O)O_(p)R^(c))R^(b))R^(b), ON═CR^(b)R^(c), ONR^(b)R^(c),S(═O)_(o)(═NR^(b))_(q)R^(c), SO₂NR^(b)(═O)NR^(b)R^(c), P(═X²)R^(b)R^(c),OP(═X²)(O_(p)R^(c))R^(b), OP(═X²)(OR^(c))₂, N═CR^(b)R^(c),NR^(b)N═CR^(b)R_(c), NR^(b)NR^(b)R^(c), NR^(b)C(═S)NR^(b)R^(c),NR^(b)C(═NR^(b))NR^(b)R^(c), NR^(b)NR^(b)C(═X²)NR^(b)R^(c), NR^(b)NR^(b)SO₂NR^(b)R^(c), or N═S(═O)_(p)R^(c)R^(c), R¹ is hydrogen, C₁-C₈-alkyl,C₂-C₈-alkenyl, C₂-C₈-alkynyl, C₃-C₁₀-cycloalkyl, C₄-C₁₀-cycloalkenyl,C₅-C₁₄-cycloalkylcycloalkyl or R¹ may form a three- to eleven-memberedsaturated, or partially unsaturated or aromatic carbo- or heterocyclicring or ring system, which may contain 1 to 4 heteroatoms selected fromN(R^(c))_(p), O, and S, wherein S may be oxidized, and wherein theaforementioned groups and the carbo- or heterocyclic rings system may beunsubstituted, partially or fully substituted with R^(a); or R¹ isC(═O)R^(b), C(═O)OR^(e), NR^(b)R^(c), C(═O)NR^(b)R^(c),C(═S)NR^(b)R^(c), SO₂NR^(b)R^(c), OC(═O)R^(c), OC(═O)OR^(e),OC(═O)NR^(b)R^(e), N(R^(c))C(═O)R^(c), N(R^(c))C(═O)OR^(e),N(R^(c))C(═O)NR^(b)R^(c), NR′SO₂R^(b), NR′SO₂NR^(b)R^(c), Si(R^(d))₃,C(═NR^(c))R^(c), C(═NOR^(c))R^(c); C(═NNR^(b)R^(c))R^(c),C(═NN(C(═O)R^(b))R^(c))R^(c), C(═NN(C═O)OR^(c))(R^(c))₂,S(═O)_(o)(═NR^(b))_(q)R^(c) or N═CR^(b)R^(c); R^(a) is eachindependently halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy,C₁-C₆-haloalkoxy, C₂-C₄-alkenyl, C₂-C₄-alkynyl, C₃-C₆-cycloalkyl, CN,OR^(c), NR^(b)R^(c), NO₂, C(═O)(O)_(p)R^(c), OC(═O)(O)_(p)R^(e),C(═O)NR^(b)R^(c), OC(═O)NR^(b)R^(e), NR^(b)C(═O)(O)_(p)R^(e),NR^(b)C(═O)NR^(b)R^(c), C(═S)NR^(b)R^(c), S(O)_(m)R^(b), SO₂NR^(b)R^(c),OSO₂R^(c), OSO₂NR^(b)R^(c), NR^(b) SO₂R^(c), NR^(b) SO₂NR^(b)R^(c),N═S(═O)_(p)R^(c)R^(c), S(═O)_(o)(═NR^(b))_(q)R^(c), SF₅, OCN, SCN,Si(R^(d))₃ or a three- to six-membered saturated, or partiallyunsaturated or aromatic carbo- or heterocyclic ring, which may contain 1to 3 heteroatoms selected from N—(R^(c))_(p), O, and S which may beoxidized, and wherein the aforementioned groups and the carbo- orheterocyclic ring may be partially or fully substituted with R^(aa), ortwo geminally bound groups R^(a) together may form a group selected fromthe group consisting of ═O, ═S, ═CR^(b)R^(c), ═NR^(c), ═NOR^(c), and═NNR^(c)R^(c); R^(aa) is each independently halogen, C₁-C₆-alkyl,C₁-C₆-haloalkyl, C₁-C₆-alkoxy or C₁-C₆-haloalkoxy; R^(b) is eachindependently hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy,C₁-C₆-haloalkoxy or a three- to six-membered saturated, or partiallyunsaturated or aromatic carbo- or heterocyclic ring, which may contain 1to 3 heteroatoms selected from N(R^(c))_(p), O, and S, wherein S may beoxidized and which carbo- or heterocyclic ring may be partially or fullysubstituted with R^(aa); R^(c) is each independently hydrogen,C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkylcarbonyl, C₁-C₆ cycloalkyl, ora three- to six-membered saturated, partially unsaturated or aromaticcarbo- or heterocyclic ring, which may contain 1 to 3 heteroatomsselected from N(R^(aa))_(p), O and S, wherein S may be oxidized andwherein the carbo- or heterocyclic ring may be partially or fullysubstituted with R^(aa); wherein two geminally bound groups R^(b)R^(b),R^(c)R^(b) or R^(c)R^(c) together with the atom to which they are bound,may form a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturatedor aromatic carbo- or heterocyclic ring, which may contain 1 to 2heteroatoms or heteroatoms groups selected from N, O, S, NO, SO and SO₂and wherein the carbo- or heterocyclic ring may be partially or fullysubstituted with R⁴; R^(d) is each independently hydrogen, phenyl,C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₈-cycloalkyl, orC₁-C₆-alkoxyalkyl, wherein the above mentioned groups may be substitutedwith one or more halogen; R^(e) is each independently, C₁-C₄-alkyl,C₁-C₄-haloalkyl, C₁-C₄-alkylcarbonyl, C₁-C₆ cycloalkyl, or a three- tosix-membered saturated, partially unsaturated or aromatic carbo- orheterocyclic ring, which may contain 1 to 3 heteroatoms selected fromN(R^(aa))_(p), O and S, wherein S may be oxidized and wherein the carbo-or heterocyclic ring may be partially or fully substituted with R^(aa);n is 0, 1 or 2; m is 0, 1, or 2; p is 0 or 1; R² is H, halogen, CN,C₁-C₈ alkyl, C₂-C₈ alkenyl, C₂-C₈ alkynyl, C₃-C₁₀ cycloalkyl, C₄-C₁₀alkylcycloalkyl, C₄-C₁₀ cycloalkylalkyl, C₆-C₁₄ cycloalkylcycloalkyl,C₅-C₁₀ or C₃-C₆ cycloalkenyl, wherein the aforementioned groups may beunsubstituted, partially, or fully substituted with R^(2a), or R² mayform a carbo- or heterocyclic three- to ten-membered ring or a seven- toeleven-membered rings system, which ring or ring system may besaturated, partially unsaturated, or aromatic, and which ring or ringsystem may contain 1 to 4 heteroatoms selected from N(R^(c))_(p), O, andS, wherein S may be oxidized, and wherein the carbo- or heterocyclicring or rings system may be unsubstituted, partially, or fullysubstituted with R^(2a); with the proviso that if R² is halogen or CN,then Z is a direct bond; R^(2a) is each independently halogen,C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,C₂-C₄-alkenyl, C₂-C₄-alkynyl, C₃-C₆-cycloalkyl, CN, OR^(c), NR^(b)R^(c),NO₂, C(═O)(O)_(p)R^(c), OC(═O)(O)_(p)R^(e), C(═O)NR^(b)R^(c),OC(═O)NR^(b)R^(e), NR^(b)C(═O)(O)_(p)R^(c), NR^(b)C(═O)NR^(b)R^(c),C(═S)NR^(b)R^(c), S(O)_(m)R^(b), SO₂NR^(b)R^(c), OSO₂R^(c),OSO₂NR^(b)R^(c), NR^(b) SO₂R^(c), NR^(b) SO₂NR^(b)R^(c), SF 5, OCN, SCN,Si(R^(d))₃, C(═N(O)_(p)R^(b)) R^(b), C(═NNR^(b)R^(c))R^(b),C(═NN(C(═O)O_(p)R^(c))R^(c))R^(b), ON═CR^(b)R^(c), ONR^(b)R^(c),S(═O)_(o)(═NR^(b))_(q)R^(c), SO₂NR^(b)(═O)NR^(b)R^(c), P(═X²)R^(b)R^(c),OP(═X²)(O_(p)R^(c))R^(b), OP(═X²)(OR^(c))₂, N═CR^(b)R^(c),NR^(b)N═CR^(b)R^(c), NR^(b)NR^(b)R^(c), NR^(b)C(═S)NR^(b)R^(c)NR^(b)C(═NR^(b))NR^(b)R^(c), NR^(b)NR^(b)C(═X²)NR^(b)R^(c),NR^(b)NR^(b)SO₂NR^(b)R^(c), N═S(═O)_(p)R^(c)R^(c), or a three- tosix-membered saturated, or partially unsaturated or aromatic carbo- orheterocyclic ring, which may contain 1 to 3 heteroatoms selected fromN—(R^(c))_(p), O, and S, wherein S may be oxidized, and wherein theaforementioned groups and the carbo- or heterocyclic ring may bepartially or fully substituted with R^(2aa) or two geminally boundgroups R^(2a) together may form a group selected from the groupconsisting of ═O, ═S, ═CR^(b)R^(c), ═NR^(c), ═NOR^(c), and═NNR^(c)R^(c); R^(2aa) is each independently halogen, C₁-C₆-alkyl,C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₂-C₄-alkenyl,C₂-C₄-alkynyl, C₃-C₆-cycloalkyl, CN, OR^(c), NR^(b)R^(c), NO₂,C(═O)(O)_(p)R^(c), OC(═O)(O)_(p)R^(e), C(═O)NR^(b)R^(c),O_(c)(═O)NR^(b)R^(e), NR^(b)C(═O)(O)_(p)R^(e), NR^(b)C(═O)NR^(b)R^(c),C(═S)NR^(b)R^(c), S(O)_(m)R^(b), SO₂NR^(b)R^(c), OSO₂R^(c),OSO₂NR^(b)R^(c), NR^(b) SO₂R^(c), NR^(b) SO₂NR^(b)R^(c), SF₅, OCN, SCN,Si(R^(d))₃, C(═N(O)_(p)R^(b))R^(b), C(═NNR^(b)R^(c))R^(b),C(═NN(C(═O)O_(p)R^(c))R^(b))R^(b), ON═CR^(b)R^(c), ONR^(b)R^(c),S(═O)_(o)(═NR^(b))_(q)R^(c), SO₂NR^(b)(═O)NR^(b)R^(c), P(═X²)R^(b)R^(c),OP(═X²)(O_(p)R^(c))R^(b), OP(═X²)(OR^(c))₂, N═CR^(b)R^(c),NR^(b)N═CR^(b)R^(c), NR^(b)NR^(b)R^(c), NR^(b)C(═S)NR^(b)R^(c)NR^(b)C(═NR^(b))NR^(b)R^(c), NR^(b)NR^(b)C(═X²)NR^(b)R^(c),NR^(b)NR^(b)SO₂NR^(b)R^(c), or N═S(═O)_(p)R^(c)R^(c) or two geminallybound groups R^(2aa) together may form a group selected from the groupconsisting of ═O, ═S,═CR^(b)R^(c), ═NR^(c), ═NOR^(c), and ═NNR^(c)R^(c);X² is independently O or S; R⁴ is each independently halogen,C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,C₂-C₄-alkenyl, C₂-C₄-alkynyl, C₃-C₆-cycloalkyl, CN, OR^(c), NR^(b)R^(c),NO₂, C(═O)(O)_(p)R^(c), OC(═O)(O)_(p)R^(e), C(═O)NR^(b)R^(c),OC(═O)NR^(b)R^(e), NR^(b)C(═O)(O)_(p)R^(e), NR^(b)C(═O)NR^(b)R^(c),C(═S)NR^(b)R^(c), S(O)_(m)R^(b), SO₂NR^(b)R^(c), OSO₂R^(c),OSO₂NR^(b)R^(c), NR^(b)SO₂R^(c), NR^(b)SO₂NR^(b)R^(c), SF₅, OCN, SCN,Si(R^(d))₃, C(═N(O)_(p)R^(b))R^(b), C(═NNR^(b)R^(c))R^(b),C(═NN(C(═O)O_(p)R^(c))R^(b))R^(b), ON═CR^(b)R^(c), ONR^(b)R^(c),S(═O)_(o)(═NR^(b))_(q)R^(c), SO₂NR^(b)(═O)NR^(b)R^(c), P(═X²)R^(b)R^(c),OP(═X²)(O_(p)R^(c))R^(b), OP(═X²)(OR^(c))₂, N═CR^(b)R^(c),NR^(b)N═CR^(b)R^(c), NR^(b)NR^(b)R^(c), NR^(b)C(═S)NR^(b)R^(c),NR^(b)C(═NR^(b))NR^(b)R^(c), NR^(b)NR^(b)C(═X²)NR^(b)R^(c),NR^(b)NR^(b)SO₂NR^(b)R^(c), or N═S(═O)_(p)R^(c)R^(c) or two geminallybound groups R⁴ together may form a group selected from the groupconsisting of ═O, ═S, ═CR^(b)R^(c), ═NR^(c), ═NOR^(c), and═NNR^(c)R^(c); or a stereoisomer, tautomer, salt, or N-oxide thereof.17. The compound of formula (I) of claim 16 or a stereoisomer, tautomer,salt, or N-oxide thereof, wherein X and Y are O.
 18. The compound offormula (I) of claim 16 or a stereoisomer, tautomer, salt, or N-oxidethereof, wherein R³ is C₁-C₄-alkyl or C₁-C₄-haloalkyl, each substitutedwith at least one substituent selected from cyano.
 19. The compound offormula (I) of claim 16 or a stereoisomer, tautomer, salt, or N-oxidethereof of, wherein A is CH or N, wherein the nitrogen of thepyrimidinium ring taken together with the contiguous linking carbon atomand A as depicted in formula (I), form a five or six membered ring,wherein each remaining ring member is selected from carbon atoms and upto one heteroatom selected from the group consisting of O, S andN(R^(c))_(p), which ring may be substituted with R^(a).
 20. The compoundof formula (I) of claim 16 or a stereoisomer, tautomer, salt, or N-oxidethereof, wherein Z is a direct bond, and R² is a six membered carbo- orheterocyclic ring, which ring may be unsubstituted, partially, or fullysubstituted with R^(2a), and wherein R^(2a) is halogen, C₁-C₆-haloalkyl,C₁-C₆-haloalkoxy, C(═O)OR^(c), C(═O)NR^(b)R^(c), phenyl, or pyridyl,which may be substituted with halogen, C₁-C₆-haloalkyl orC₁-C₆-haloalkoxy.
 21. The compound of formula (I) of claim 16 or astereoisomer, tautomer, salt, or N-oxide thereof, wherein Z is a directbond, and R² is phenyl, which is optionally substituted with halogen,C₁-C₄-haloalkyl, and/or C₁-C₄-haloalkoxy.
 22. The compound of formula(I) of claim 16 or a stereoisomer, tautomer, salt, or N-oxide thereof,wherein R¹ is C₁-C₄-alkyl, C₃-C₆-cycloalkyl, C₂-C₄-alkenyl, benzyl orphenyl, which groups may be partially or fully substituted with halogenor C₁-C₄-alkyl.
 23. The compound of formula (I) of claim 18 or astereoisomer, tautomer, salt, or N-oxide thereof, wherein X, Y are eachO; A is CH and the nitrogen of the pyrimidinium ring taken together withthe contiguous linking carbon atom and A as depicted in formula (I),form a five or six membered ring, wherein each remaining ring member isselected from 2 and 3 carbon atoms; R¹ is CH₃, CH₂CH₃, isopropyl,cyclopropyl, CH₂CF₃, phenyl, allyl or benzyl; R² is phenyl which may besubstituted with halogen, C₁-C₆-haloalkyl, C₁-C₆-haloalkoxy or phenyl; Zis a direct bond and R³ is cyanoethyl or cyanomethyl.
 24. A compositioncomprising at least one compound of formula (I) of claim 16 and at leastone inert liquid and/or solid carrier.
 25. A method for protectingcrops, plants, plant propagation material and/or growing plants fromattack or infestation by invertebrate pests comprising contacting ortreating the crops, plants, plant propagation material and growingplants, or soil, material, surface, space, area or water in which thecrops, plants, plant propagation material is stored or the plant isgrowing with a pesticidally effective amount of at least one compound offormula (I) of claim 16 or a stereoisomer, tautomer, salt, or N-oxidethereof.
 26. A method for combating, controlling, preventing orprotecting against infestation or infection by invertebrate pest, whichmethod comprises contacting said pest or its food supply, habitat orbreeding grounds with a pesticidally effective amount of at least onecompound of formula (I) of claim 16 or a stereoisomer, tautomer, salt,or N-oxide thereof.
 27. A non-therapeutic method for treating animalsinfested or infected by parasites or preventing animals of gettinginfected or infested by parasites or protecting animals againstinfestation or infection by parasites which comprises orally, topicallyor parenterally administering or applying to the animals aparasiticidally effective amount of a compound of formula (I) of claim16 or a stereoisomer, tautomer, salt, or N-oxide thereof.
 28. A seedcomprising a compound of formula (I) of claim 16 or a stereoisomer,tautomer, salt, or N-oxide thereof in an amount of from 0.1 g to 10 kgper 100 kg of seed.
 29. The compound of formula (I) of claim 18 or astereoisomer, tautomer, salt, or N-oxide thereof, wherein the cyano isCH₂—CN or CH₂—CH₂—CN.
 30. The compound of formula (I) of claim 18 or astereoisomer, tautomer, salt, or N-oxide thereof, wherein the cyano isCH₂—CN.
 31. The compound of formula (I) of claim 17 or a stereoisomer,tautomer, salt, or N-oxide thereof, wherein A is CH or N, wherein thenitrogen of the pyrimidinium ring taken together with the contiguouslinking carbon atom and A as depicted in formula (I), form a five or sixmembered ring, wherein each remaining ring member is selected fromcarbon atoms and up to one heteroatom selected from the group consistingof O, S and N(R^(c))_(p), which ring may be substituted with R^(a). 32.The compound of formula (I) of claim 17 or a stereoisomer, tautomer,salt, or N-oxide thereof, wherein Z is a direct bond, and R² is a sixmembered carbo- or heterocyclic ring, which ring may be unsubstituted,partially, or fully substituted with R^(2a), and wherein R^(2a) ishalogen, C₁-C₆-haloalkyl, C₁-C₆-haloalkoxy, OR^(c), C(═O)OR^(c),C(═O)NR^(b)R^(c), phenyl, or pyridyl, which may be substituted withhalogen, C₁-C₆-haloalkyl or C₁-C₆-haloalkoxy.
 33. The compound offormula (I) of claim 17 or a stereoisomer, tautomer, salt, or N-oxidethereof, wherein Z is a direct bond, and R² is phenyl, which isoptionally substituted with halogen, C₁-C₄-haloalkyl, and/orC₁-C₄-haloalkoxy.
 34. A method for combating, controlling, preventing orprotecting against infestation or infection by invertebrate pest, whichmethod comprises contacting said pest or its food supply, habitat orbreeding grounds with a pesticidally effective amount of at least onecompound of formula (I) or a stereoisomer, tautomer, salt, or N-oxidethereof a composition of claim
 24. 35. A method for protecting crops,plants, plant propagation material and/or growing plants from attack orinfestation by invertebrate pests comprising contacting or treating thecrops, plants, plant propagation material and growing plants, or soil,material, surface, space, area or water in which the crops, plants,plant propagation material is stored or the plant is growing with acomposition of claim 24.